Mayr's Database Of Reactivity Parameters
AK Prof. Mayr

C-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles
Found 572 Molecules.
Molecule Solvent Reactivity Parameters Classification Reference (sort by title or year)
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5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)
THFN  Parameter: 31.92
sN Parameter: 0.52
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)
DMSON  Parameter: 30.82
sN Parameter: 0.41
**Tetrahedron 2019, 75, 459-463
DOI: 10.1016/j.tet.2018.11.075
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1,3-Diisopropyl-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)
THFN  Parameter: 30.25
sN Parameter: 0.54
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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cyano((diphenylmethylene)amino)methanide
DMSON  Parameter: 29.50
sN Parameter: 0.50
*Tetrahedron 2019, 75, 459-463
DOI: 10.1016/j.tet.2018.11.075
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1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
DMSON  Parameter: 29.10
sN Parameter: 0.50
*Tetrahedron 2019, 75, 459-463
DOI: 10.1016/j.tet.2018.11.075
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1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
DMSON  Parameter: 29.02
sN Parameter: 0.49
**Tetrahedron 2019, 75, 459-463
DOI: 10.1016/j.tet.2018.11.075
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anion of 2-phenyl-propionitrile (in DMSO)
DMSON  Parameter: 28.95
sN Parameter: 0.58
***J. Org. Chem. 2009, 74, 75-81
DOI: 10.1021/jo802241x
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chloro(phenylsulfonyl)methanide (in DMSO)
DMSON  Parameter: 28.27
sN Parameter: 0.42
***J. Org. Chem. 2017, 82, 2011-2017
DOI: 10.1021/acs.joc.6b02844
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2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)
DMSON  Parameter: 27.77
sN Parameter: 0.47
***Tetrahedron 2019, 75, 459-463
DOI: 10.1016/j.tet.2018.11.075
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2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)
DMSON  Parameter: 27.62
sN Parameter: 0.53
***Eur. J. Org. Chem. 2013, , 4255-4261
DOI: 10.1002/ejoc.201300265
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2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)
DMSON  Parameter: 27.57
sN Parameter: 0.53
***Eur. J. Org. Chem. 2013, , 4255-4261
DOI: 10.1002/ejoc.201300265
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2-PhCH(-)CO2Et (in DMSO)
DMSON  Parameter: 27.54
sN Parameter: 0.57
***Eur. J. Org. Chem. 2013, , 4255-4261
DOI: 10.1002/ejoc.201300265
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2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
DMSON  Parameter: 27.45
sN Parameter: 0.38
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)
DMSON  Parameter: 27.28
sN Parameter: 0.50
***J. Org. Chem. 2009, 74, 75-81
DOI: 10.1021/jo802241x
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1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
DMSON  Parameter: 26.95
sN Parameter: 0.52
***Tetrahedron 2019, 75, 459-463
DOI: 10.1016/j.tet.2018.11.075
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chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)
DMSON  Parameter: 26.90
sN Parameter: 0.45
***J. Org. Chem. 2017, 82, 2011-2017
DOI: 10.1021/acs.joc.6b02844
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2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
DMSON  Parameter: 26.71
sN Parameter: 0.37
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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chloro(phenylsulfonyl)methanide (in DMF)
DMFN  Parameter: 26.64
sN Parameter: 0.64
-Chem. Eur. J. 2008, 14, 6108-6118
DOI: 10.1002/chem.200800329
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1-mesityl-3-methyl-5-methylene-2,4,6-triphenyl-2,5-dihydropyridin-1-ium-2-ide (in THF)
THFN  Parameter: 26.16
sN Parameter: 0.52
***Angew. Chem. Int. Ed. 2024, , e202318283
DOI: 10.1002/anie.202318283
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cyano(pyridin-1-ium-1-yl)methanide (in DMSO)
DMSON  Parameter: 25.94
sN Parameter: 0.42
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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anion of (benzylsulfonyl)benzene (in DMSO)
DMSON  Parameter: 25.77
sN Parameter: 0.56
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
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chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)
DMSON  Parameter: 25.59
sN Parameter: 0.51
***J. Org. Chem. 2017, 82, 2011-2017
DOI: 10.1021/acs.joc.6b02844
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enolate of 3-isochromanone (in DMSO)
DMSON  Parameter: 25.39
sN Parameter: 0.54
***J. Org. Chem. 2024, 89, 6915-6928
DOI: 10.1021/acs.joc.4c00277
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anion of 2-(4-CN-C6H4)propionitrile (in DMSO)
DMSON  Parameter: 25.35
sN Parameter: 0.56
***J. Org. Chem. 2009, 74, 75-81
DOI: 10.1021/jo802241x
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anion of 4-cyanobenzyl-CN (in DMSO)
DMSON  Parameter: 25.11
sN Parameter: 0.54
***J. Org. Chem. 2009, 74, 75-81
DOI: 10.1021/jo802241x
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anion of 1-phenylpropan-2-one (in DMSO)
DMSON  Parameter: 24.99
sN Parameter: 0.60
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
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chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)
DMSON  Parameter: 24.88
sN Parameter: 0.49
***J. Org. Chem. 2017, 82, 2011-2017
DOI: 10.1021/acs.joc.6b02844
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1,3-bis(2,6-diisopropylphenyl)-5-methyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)
THFN  Parameter: 24.86
sN Parameter: 0.52
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO)
DMSON  Parameter: 24.30
sN Parameter: 0.51
***Org. Biomol. Chem. 2008, 6, 3052-3058
DOI: 10.1039/b805604h
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potassium indenide (in DMSO)
DMSON  Parameter: 24.16
sN Parameter: 0.68
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
DOI: 10.1002/anie.201501385
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bromo(phenylsulfonyl)methanide (in DMSO)
DMSON  Parameter: 23.90
sN Parameter: 0.62
***J. Org. Chem. 2017, 82, 2011-2017
DOI: 10.1021/acs.joc.6b02844
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sodium indenide (in DMSO)
DMSON  Parameter: 23.74
sN Parameter: 0.71
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
DOI: 10.1002/anie.201501385
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lithium indenide (in DMSO)
DMSON  Parameter: 23.66
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
DOI: 10.1002/anie.201501385
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2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)
DMSON  Parameter: 23.64
sN Parameter: 0.65
***Eur. J. Org. Chem. 2013, , 4255-4261
DOI: 10.1002/ejoc.201300265
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1,3-Bis(2,6-diisopropylphenyl)-5-(4-methoxyphenyl)-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)
THFN  Parameter: 23.55
sN Parameter: 0.56
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)
THFN  Parameter: 23.35
sN Parameter: 0.40
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
DOI: 10.1002/anie.201102435
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2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)
DMSON  Parameter: 23.27
sN Parameter: 0.70
***Eur. J. Org. Chem. 2013, , 4255-4261
DOI: 10.1002/ejoc.201300265
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anion of 1,2-diphenylethanone (in DMSO)
DMSON  Parameter: 23.15
sN Parameter: 0.60
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
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anion of diethyl 2-butylmalonate (in DMSO)
DMSON  Parameter: 23.00
sN Parameter: 0.55
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
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3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)
THFN  Parameter: 23.00
sN Parameter: 0.46
***Org. Lett. 2016, 18, 3566-3569
DOI: 10.1021/acs.orglett.6b01525
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1,3-bis(2,6-diisopropylphenyl)-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)
THFN  Parameter: 22.80
sN Parameter: 0.60
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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anion of (4-CN-C6H4)CH2SO2Ph (in DMSO)
DMSON  Parameter: 22.60
sN Parameter: 0.57
***Org. Biomol. Chem. 2008, 6, 3052-3058
DOI: 10.1039/b805604h
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1,3-Bis(2,6-diisopropylphenyl)-4-methylene-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)
THFN  Parameter: 22.30
sN Parameter: 0.49
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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anion of nitroethane (in DMF)
DMFN  Parameter: 22.21
sN Parameter: 0.48
***Chem. Eur. J. 2008, 14, 6108-6118
DOI: 10.1002/chem.200800329
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1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)
THFN  Parameter: 21.72
sN Parameter: 0.45
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
DOI: 10.1002/anie.201102435
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1-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
DMSON  Parameter: 21.61
sN Parameter: 0.58
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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anion of nitroethane (in DMSO)
DMSON  Parameter: 21.54
sN Parameter: 0.62
***J. Org. Chem. 2003, 68, 6880-6886
DOI: 10.1021/jo0344182
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3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF)
THFN  Parameter: 21.50
sN Parameter: 0.45
***Org. Lett. 2016, 18, 3566-3569
DOI: 10.1021/acs.orglett.6b01525
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1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)
THFN  Parameter: 21.36
sN Parameter: 0.42
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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Me2S(O)=CH2 (in DMSO)
DMSON  Parameter: 21.29
sN Parameter: 0.47
***J. Am. Chem. Soc. 2010, 132, 17894-17900
DOI: 10.1021/ja1084749
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1,3,5-trimethyl-2-methylene-1,2-dihydropyridine (in DMSO)
DMSON  Parameter: 21.16
sN Parameter: 0.59
***Eur. J. Org. Chem. 2024, , EarlyView
DOI: 10.1002/ejoc.202400373
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anion of diethyl methylmalonate (in DMSO)
DMSON  Parameter: 21.13
sN Parameter: 0.68
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
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Me2S=CH(4-CN-C6H4) (in DMSO)
DMSON  Parameter: 21.07
sN Parameter: 0.68
***J. Am. Chem. Soc. 2010, 132, 17894-17900
DOI: 10.1021/ja1084749
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1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)
THFN  Parameter: 20.78
sN Parameter: 0.61
***Angew. Chem. Int. Ed. 2023, 62, e202309790
DOI: 10.1002/anie.202309790
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1,6-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)
DMSON  Parameter: 20.76
sN Parameter: 0.60
***Eur. J. Org. Chem. 2024, , EarlyView
DOI: 10.1002/ejoc.202400373
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anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN)
MeOH-MeCN mixN  Parameter: 20.72
sN Parameter: 0.58
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
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anion of nitromethane (in DMSO)
DMSON  Parameter: 20.71
sN Parameter: 0.60
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
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1,3-diethoxy-2-fluoro-1,3-dioxopropan-2-ide (in DMSO)
DMSON  Parameter: 20.63
sN Parameter: 0.76
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
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anion of 2-nitropropane (in DMSO)
DMSON  Parameter: 20.61
sN Parameter: 0.69
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
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MeSO-CH-CO2Et (in DMSO)
DMSON  Parameter: 20.61
sN Parameter: 0.64
***Chem. Eur. J. 2010, 16, 8610-8614
DOI: 10.1002/chem.201001455
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1-(ethoxycarbonyl)-2-oxocyclododecan-1-ide (in DMSO)
DMSON  Parameter: 20.60
sN Parameter: 0.63
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
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2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)
DMSON  Parameter: 20.51
sN Parameter: 0.64
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
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3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)
THFN  Parameter: 20.41
sN Parameter: 0.46
***Org. Lett. 2016, 18, 3566-3569
DOI: 10.1021/acs.orglett.6b01525
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2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO)
DMSON  Parameter: 20.24
sN Parameter: 0.60
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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anion of diethyl malonate (in DMSO)
DMSON  Parameter: 20.22
sN Parameter: 0.65
***Angew. Chem. Int. Ed. 2002, 41, 91-95
DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P
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anion of 4-nitrobenzyl-CN (in MeCN)
MeCNN  Parameter: 20.10
sN Parameter: 0.71
***J. Am. Chem. Soc. 2020, 142, 8383-8402
DOI: 10.1021/jacs.0c01960
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1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
DMSON  Parameter: 20.08
sN Parameter: 0.57
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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1,2,3-trimethoxy-1,3-dioxopropan-2-ide (in DMSO)
DMSON  Parameter: 20.08
sN Parameter: 0.74
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
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1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO)
DMSON  Parameter: 20.02
sN Parameter: 0.76
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
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2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO)
DMSON  Parameter: 20.00
sN Parameter: 0.71
***Eur. J. Org. Chem. 2013, , 4255-4261
DOI: 10.1002/ejoc.201300265
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bis(4-nitrophenyl)methanide (in DMSO)
DMSON  Parameter: 19.92
sN Parameter: 0.67
***ARKIVOC 2008, (x), 37-53
DOI: 10.3998/ark.5550190.0009.a05
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1,3-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)
DMSON  Parameter: 19.91
sN Parameter: 0.62
***Eur. J. Org. Chem. 2024, , EarlyView
DOI: 10.1002/ejoc.202400373
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anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN)
MeCNN  Parameter: 19.90
sN Parameter: 0.66
***J. Am. Chem. Soc. 2020, 142, 8383-8402
DOI: 10.1021/jacs.0c01960
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1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole
THFN  Parameter: 19.84
sN Parameter: 0.58
***J. Org. Chem. 2021, 86, 2974-2985
DOI: 10.1021/acs.joc.0c02838
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1,3-dimethyl-2-methylene-1,2-dihydropyridine (in MeCN)
MeCNN  Parameter: 19.69
sN Parameter: 0.61
***Eur. J. Org. Chem. 2024, , EarlyView
DOI: 10.1002/ejoc.202400373
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anion of 4-nitrobenzyl-CN (in DMSO)
DMSON  Parameter: 19.67
sN Parameter: 0.68
***J. Org. Chem. 2009, 74, 75-81
DOI: 10.1021/jo802241x
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anion of ethyl cyanoacetate (in DMSO)
DMSON  Parameter: 19.62
sN Parameter: 0.67
***Angew. Chem. Int. Ed. 2002, 41, 91-95
DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P
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anion of 2-(4-NO2-C6H4)propionitrile (in DMSO)
DMSON  Parameter: 19.61
sN Parameter: 0.60
***J. Org. Chem. 2009, 74, 75-81
DOI: 10.1021/jo802241x
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enolate of 2-coumaranone (in DMSO)
DMSON  Parameter: 19.60
sN Parameter: 0.75
***J. Org. Chem. 2024, 89, 6915-6928
DOI: 10.1021/acs.joc.4c00277
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1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO)
DMSON  Parameter: 19.58
sN Parameter: 0.73
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
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1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide
DMSON  Parameter: 19.53
sN Parameter: 0.83
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
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anion of malononitrile (in water)
waterN  Parameter: 19.50
sN Parameter: 0.55
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
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anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN)
MeOH-MeCN mixN  Parameter: 19.49
sN Parameter: 0.63
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
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2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
DMSON  Parameter: 19.46
sN Parameter: 0.58
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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1-methyl-2-methylene-3-phenyl-1,2-dihydropyridine (in DMSO)
DMSON  Parameter: 19.41
sN Parameter: 0.61
***Eur. J. Org. Chem. 2024, , EarlyView
DOI: 10.1002/ejoc.202400373
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2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO)
DMSON  Parameter: 19.38
sN Parameter: 0.50
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
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anion of malononitrile (in DMSO)
DMSON  Parameter: 19.36
sN Parameter: 0.67
***Angew. Chem. Int. Ed. 2002, 41, 91-95
DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P
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1-(4-(tert-butyl)phenyl)-2-methylene-4,6-diphenyl-1,2-dihydropyridine (in DMSO)
DMSON  Parameter: 19.36
sN Parameter: 0.68
***Eur. J. Org. Chem. 2024, , EarlyView
DOI: 10.1002/ejoc.202400373
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anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO)
DMSON  Parameter: 19.35
sN Parameter: 0.67
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
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anion of N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO)
DMSON  Parameter: 19.28
sN Parameter: 0.65
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
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(EtO)2P(O)CH(-)CO2Et (in DMSO)
DMSON  Parameter: 19.23
sN Parameter: 0.65
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
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anion of diethyl 2-cyclohexylmalonate (in DMSO)
DMSON  Parameter: 19.23
sN Parameter: 0.67
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
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Ph2P(O)CH(-)CO2Et (in DMSO)
DMSON  Parameter: 19.20
sN Parameter: 0.69
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
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2-ethoxy-1-methoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)
DMSON  Parameter: 19.15
sN Parameter: 0.59
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)
DMSON  Parameter: 19.03
sN Parameter: 0.58
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

(cyclohexen-1-yl)prolinate (in MeCN)
MeCNN  Parameter: 18.86
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2010, 49, 9526-9529
DOI: 10.1002/anie.201004344
image of molecule

anion of ethyl acetylacetate (in DMSO)
DMSON  Parameter: 18.82
sN Parameter: 0.69
***Angew. Chem. Int. Ed. 2002, 41, 91-95
DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P
image of molecule

2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)
DMSON  Parameter: 18.81
sN Parameter: 0.59
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

anion of diethyl 2-(isopropyl)malonate (in DMSO)
DMSON  Parameter: 18.74
sN Parameter: 0.71
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

Ph2P(O)CH(-)CN (in DMSO)
DMSON  Parameter: 18.69
sN Parameter: 0.72
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
image of molecule

1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)
THFN  Parameter: 18.68
sN Parameter: 0.63
***J. Org. Chem. 2021, 86, 2974-2985
DOI: 10.1021/acs.joc.0c02838
image of molecule

anion of benzyl trifluoromethyl sulfone (in DMSO)
DMSON  Parameter: 18.67
sN Parameter: 0.68
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
image of molecule

1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO)
DMSON  Parameter: 18.63
sN Parameter: 0.82
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
image of molecule

anion of ethyl cyanoacetate (in 91M9AN)
MeOH-MeCN mixN  Parameter: 18.59
sN Parameter: 0.65
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

(EtO)2P(O)CH(-)CN (in DMSO)
DMSON  Parameter: 18.57
sN Parameter: 0.66
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
image of molecule

anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO)
DMSON  Parameter: 18.50
sN Parameter: 0.75
***Org. Biomol. Chem. 2008, 6, 3052-3058
DOI: 10.1039/b805604h
image of molecule

Me2S=CH(p-NO2-C6H4) (in DMSO)
DMSON  Parameter: 18.42
sN Parameter: 0.65
***J. Am. Chem. Soc. 2010, 132, 17894-17900
DOI: 10.1021/ja1084749
image of molecule

anion of 3-methyl acetylacetone (in DMSO)
DMSON  Parameter: 18.38
sN Parameter: 0.72
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO)
DMSON  Parameter: 18.32
sN Parameter: 0.84
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
image of molecule

anion of p-tolylnitromethane (in DMSO)
DMSON  Parameter: 18.31
sN Parameter: 0.76
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

anion of phenylnitromethane (in DMSO)
DMSON  Parameter: 18.29
sN Parameter: 0.71
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

anion of dimethyl malonate (in 91M9AN)
MeOH-MeCN mixN  Parameter: 18.24
sN Parameter: 0.64
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)
MeOH-MeCN mixN  Parameter: 18.24
sN Parameter: 0.66
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
image of molecule

anion of malononitrile (in 91M9AN)
MeOH-MeCN mixN  Parameter: 18.21
sN Parameter: 0.69
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)
DMSON  Parameter: 18.19
sN Parameter: 0.74
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

1,3-dimethyl-2-methyleneimidazolidine (in THF)
THFN  Parameter: 18.11
sN Parameter: 0.68
***J. Org. Chem. 2021, 86, 2974-2985
DOI: 10.1021/acs.joc.0c02838
image of molecule

(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO)
DMSON  Parameter: 18.10
sN Parameter: 0.46
**Angew. Chem. Int. Ed. 2015, 54, 12497-12500
DOI: 10.1002/anie.201501385
image of molecule

anion of (3-nitrophenyl)nitromethane (in DMSO)
DMSON  Parameter: 18.06
sN Parameter: 0.71
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

MeSO2-CH-CO2Et (in DMSO)
DMSON  Parameter: 18.00
sN Parameter: 0.66
***Chem. Eur. J. 2010, 16, 8610-8614
DOI: 10.1002/chem.201001455
image of molecule

1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
DMSON  Parameter: 17.98
sN Parameter: 0.63
***J. Am. Chem. Soc. 2013, 135, 15216-15224
DOI: 10.1021/ja407885h
image of molecule

1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)
THFN  Parameter: 17.80
sN Parameter: 0.79
***J. Org. Chem. 2021, 86, 2974-2985
DOI: 10.1021/acs.joc.0c02838
image of molecule

anion of diethyl methylmalonate (in water)
waterN  Parameter: 17.68
sN Parameter: 0.50
*J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

anion of acetylacetone (in DMSO)
DMSON  Parameter: 17.64
sN Parameter: 0.73
***Angew. Chem. Int. Ed. 2002, 41, 91-95
DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P
image of molecule

anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)
DMSON  Parameter: 17.52
sN Parameter: 0.74
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
image of molecule

anion of 1,3-diphenylpropane-1,3-dione (in DMSO)
DMSON  Parameter: 17.46
sN Parameter: 0.65
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
image of molecule

fluorobis(phenylsulfonyl)methanide (in DMSO)
DMSON  Parameter: 17.46
sN Parameter: 0.73
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

1,3-dimethylbarbiturate anion (in DMSO)
DMSON  Parameter: 17.46
sN Parameter: 0.72
***J. Org. Chem. 2017, 82, 8476-8488
DOI: 10.1021/acs.joc.7b01223
image of molecule

Desoxy Breslow intermediate 2a
DMSON  Parameter: 17.41
sN Parameter: 0.74
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
DOI: 10.1002/anie.201202327
image of molecule

2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)
DMSON  Parameter: 17.36
sN Parameter: 0.71
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO)
DMSON  Parameter: 17.33
sN Parameter: 0.74
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
image of molecule

methoxybis(phenylsulfonyl)methanide (in DMSO)
DMSON  Parameter: 17.29
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)
DMSON  Parameter: 17.19
sN Parameter: 0.56
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
image of molecule

Desoxy Breslow intermediate 2a
THFN  Parameter: 17.12
sN Parameter: 0.80
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
DOI: 10.1002/anie.201202327
image of molecule

3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)
DMSON  Parameter: 17.00
sN Parameter: 0.74
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
image of molecule

anion of (4-cyanophenyl)nitromethane (in DMSO)
DMSON  Parameter: 16.96
sN Parameter: 0.73
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

anion of diethyl 2-(p-anisyl)malonate (in DMSO)
DMSON  Parameter: 16.73
sN Parameter: 0.91
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

MeO-Breslow 1c
THFN  Parameter: 16.61
sN Parameter: 0.68
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
DOI: 10.1002/anie.201204524
image of molecule

anion of 3-oxo-3-phenylpropanenitrile (in DMSO)
DMSON  Parameter: 16.55
sN Parameter: 0.78
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
image of molecule

3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)
THFN  Parameter: 16.54
sN Parameter: 0.47
***Org. Lett. 2016, 18, 3566-3569
DOI: 10.1021/acs.orglett.6b01525
image of molecule

1-(N-pyrrolidino)cyclohexene (in MeCN)
MeCNN  Parameter: 16.42
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2010, 49, 9526-9529
DOI: 10.1002/anie.201004344
image of molecule

anion of (4-nitrophenyl)nitromethane (in DMSO)
DMSON  Parameter: 16.29
sN Parameter: 0.75
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO)
DMSON  Parameter: 16.28
sN Parameter: 0.75
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
image of molecule

anion of dimedone (in DMSO)
DMSON  Parameter: 16.27
sN Parameter: 0.77
***Angew. Chem. Int. Ed. 2002, 41, 91-95
DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P
image of molecule

cyanide (in MeCN)
MeCNN  Parameter: 16.27
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2005, 44, 142-145
DOI: 10.1002/anie.200461640
image of molecule

1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)
DMSON  Parameter: 16.26
sN Parameter: 0.83
***J. Am. Chem. Soc. 2018, 140, 11474-11486
DOI: 10.1021/jacs.8b07147
image of molecule

Me2S=CH-CN (in DMSO)
DMSON  Parameter: 16.23
sN Parameter: 0.60
***Chem. Eur. J. 2010, 16, 8610-8614
DOI: 10.1002/chem.201001455
image of molecule

anion of diethyl malonate (in water)
waterN  Parameter: 16.15
sN Parameter: 0.66
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)
MeCNN  Parameter: 16.15
sN Parameter: 0.99
***J. Am. Chem. Soc. 2020, 142, 8383-8402
DOI: 10.1021/jacs.0c01960
image of molecule

2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)
DMSON  Parameter: 16.06
sN Parameter: 0.69
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

anion of 1-phenylbutane-1,3-dione (in DMSO)
DMSON  Parameter: 16.03
sN Parameter: 0.86
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
image of molecule

anion of ethyl acetylacetate (in water)
waterN  Parameter: 15.99
sN Parameter: 0.62
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)
DMSON  Parameter: 15.97
sN Parameter: 0.72
***Eur. J. Org. Chem. 2017, , 1196-1202
DOI: 10.1002/ejoc.201601513
image of molecule

anion of diethyl 2-phenylmalonate (in DMSO)
DMSON  Parameter: 15.93
sN Parameter: 0.99
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)
THFN  Parameter: 15.92
sN Parameter: 0.72
***Angew. Chem. Int. Ed. 2013, 52, 11163-11167
DOI: 10.1002/ange.201303524
image of molecule

1-(N-pyrrolidino)cyclopentene
dichloromethaneN  Parameter: 15.91
sN Parameter: 0.86
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

Me2S=CH-CO2Et (in DMSO)
DMSON  Parameter: 15.85
sN Parameter: 0.61
***Chem. Eur. J. 2010, 16, 8610-8614
DOI: 10.1002/chem.201001455
image of molecule

anion of ethyl 2-cyano-2-phenylacetate (in DMSO)
DMSON  Parameter: 15.85
sN Parameter: 1.04
***Eur. J. Org. Chem. 2017, , 1196-1202
DOI: 10.1002/ejoc.201601513
image of molecule

(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)
DMSON  Parameter: 15.68
sN Parameter: 0.65
***J. Am. Chem. Soc. 2010, 132, 17894-17900
DOI: 10.1021/ja1084749
image of molecule

bis(phenylsulfonyl)methanide (in DMSO)
DMSON  Parameter: 15.68
sN Parameter: 0.74
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
DOI: 10.1002/anie.201605616
image of molecule

MeO-Breslow 1e
THFN  Parameter: 15.65
sN Parameter: 0.52
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
DOI: 10.1002/anie.201204524
image of molecule

anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)
MeCNN  Parameter: 15.62
sN Parameter: 0.99
***J. Am. Chem. Soc. 2020, 142, 8383-8402
DOI: 10.1021/jacs.0c01960
image of molecule

(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO)
DMSON  Parameter: 15.60
sN Parameter: 0.51
**Angew. Chem. Int. Ed. 2015, 54, 12497-12500
DOI: 10.1002/anie.201501385
image of molecule

barbiturate anion (in DMSO)
DMSON  Parameter: 15.59
sN Parameter: 0.80
***J. Org. Chem. 2017, 82, 8476-8488
DOI: 10.1021/acs.joc.7b01223
image of molecule

Dexoxy Breslow intermediate 6
THFN  Parameter: 15.58
sN Parameter: 0.57
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
DOI: 10.1002/anie.201204524
image of molecule

anion of 2-phenylmalononitrile (in DMSO)
DMSON  Parameter: 15.58
sN Parameter: 1.00
***Eur. J. Org. Chem. 2017, , 1196-1202
DOI: 10.1002/ejoc.201601513
image of molecule

anion of ethyl cyanoacetate (in water)
waterN  Parameter: 15.57
sN Parameter: 0.58
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)
THFN  Parameter: 15.33
sN Parameter: 0.79
***Angew. Chem. Int. Ed. 2013, 52, 11163-11167
DOI: 10.1002/ange.201303524
image of molecule

anion of triethyl methanetricarboxylate (in DMSO)
DMSON  Parameter: 15.33
sN Parameter: 0.72
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

3-pyrrolidino-1H-indene (in MeCN)
MeCNN  Parameter: 15.27
sN Parameter: 0.93
***Synthesis 2019, 51, 1157-1170
DOI: 10.1055/s-0037-1611634
image of molecule

anion of ethyl 2-nitroacetate (in DMSO)
DMSON  Parameter: 15.24
sN Parameter: 0.74
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
image of molecule

5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
DMSON  Parameter: 15.13
sN Parameter: 0.75
***Chem. Eur. J. 2014, 20, 11069-11077
DOI: 10.1002/chem.201403161
image of molecule

anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)
DMSON  Parameter: 15.07
sN Parameter: 0.79
***Eur. J. Org. Chem. 2017, , 1196-1202
DOI: 10.1002/ejoc.201601513
image of molecule

1-(N-piperidino)cyclopentene
dichloromethaneN  Parameter: 15.06
sN Parameter: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
DMSON  Parameter: 15.02
sN Parameter: 0.75
***Chem. Eur. J. 2014, 20, 11069-11077
DOI: 10.1002/chem.201403161
image of molecule

anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)
DMSON  Parameter: 14.99
sN Parameter: 0.83
***Eur. J. Org. Chem. 2017, , 1196-1202
DOI: 10.1002/ejoc.201601513
image of molecule

methyl (cyclohexen-1-yl)prolinate (in MeCN)
MeCNN  Parameter: 14.96
sN Parameter: 0.68
***Angew. Chem. Int. Ed. 2010, 49, 9526-9529
DOI: 10.1002/anie.201004344
image of molecule

anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO)
DMSON  Parameter: 14.94
sN Parameter: 0.96
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

1-(N-pyrrolidino)cyclohexene
dichloromethaneN  Parameter: 14.91
sN Parameter: 0.86
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

1,3-diethyl-thiobarbiturate anion (in DMSO)
DMSON  Parameter: 14.90
sN Parameter: 0.80
***J. Org. Chem. 2017, 82, 8476-8488
DOI: 10.1021/acs.joc.7b01223
image of molecule

MeO-Breslow 1a
THFN  Parameter: 14.77
sN Parameter: 0.80
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
DOI: 10.1002/anie.201204524
image of molecule

anion of (3-nitrophenyl)nitromethane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 14.75
sN Parameter: 0.71
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)
DMSON  Parameter: 14.49
sN Parameter: 0.86
***J. Am. Chem. Soc. 2007, 129, 9753-9761
DOI: 10.1021/ja072135b
image of molecule

(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)
DMSON  Parameter: 14.48
sN Parameter: 0.71
***J. Am. Chem. Soc. 2010, 132, 17894-17900
DOI: 10.1021/ja1084749
image of molecule

5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
DMSON  Parameter: 14.48
sN Parameter: 0.86
***Chem. Eur. J. 2014, 20, 11069-11077
DOI: 10.1002/chem.201403161
image of molecule

3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO)
DMSON  Parameter: 14.46
sN Parameter: 0.91
***Eur. J. Org. Chem. 2015, , 7594-7601
DOI: 10.1002/ejoc.201501107
image of molecule

Desoxy Breslow intermediate 2a'
THFN  Parameter: 14.45
sN Parameter: 0.71
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
DOI: 10.1002/anie.201202327
image of molecule

(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in DMSO)
DMSON  Parameter: 14.40
sN Parameter: 0.64
***Angew. Chem. Int. Ed. 2013, 52, 11163-11167
DOI: 10.1002/ange.201303524
image of molecule

(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)
THFN  Parameter: 14.40
sN Parameter: 0.66
***Angew. Chem. Int. Ed. 2013, 52, 11163-11167
DOI: 10.1002/ange.201303524
image of molecule

anion of 3-methyl acetylacetone (in water)
waterN  Parameter: 14.33
sN Parameter: 0.69
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

anion of (3-nitrophenyl)nitromethane (in water)
waterN  Parameter: 14.25
sN Parameter: 0.46
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

2-thiobarbiturate anion (in DMSO)
DMSON  Parameter: 14.24
sN Parameter: 0.82
***J. Org. Chem. 2017, 82, 8476-8488
DOI: 10.1021/acs.joc.7b01223
image of molecule

1-pyrrolidino-3,4-dihydronaphthalene (in MeCN)
MeCNN  Parameter: 14.09
sN Parameter: 0.66
***Synthesis 2019, 51, 1157-1170
DOI: 10.1055/s-0037-1611634
image of molecule

1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)
THFN  Parameter: 14.07
sN Parameter: 0.84
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
DOI: 10.1002/anie.201102435
image of molecule

anion of (4-nitrophenyl)nitromethane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 14.05
sN Parameter: 0.72
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

anion of nitromethane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 14.02
sN Parameter: 0.61
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

1-(N-piperidino)cyclohexene (in MeCN)
MeCNN  Parameter: 14.02
sN Parameter: 0.76
***J. Am. Chem. Soc. 2013, 135, 6579-6587
DOI: 10.1021/ja401106x
image of molecule

(C6H5)-(CO)-CH=SMe2 (in DMSO)
DMSON  Parameter: 13.95
sN Parameter: 0.69
***J. Am. Chem. Soc. 2010, 132, 17894-17900
DOI: 10.1021/ja1084749
image of molecule

anion of (4-cyanophenyl)nitromethane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.92
sN Parameter: 0.74
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

anion of Meldrums acid (in DMSO)
DMSON  Parameter: 13.91
sN Parameter: 0.86
***Angew. Chem. Int. Ed. 2002, 41, 91-95
DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P
image of molecule

Desoxy Breslow intermediate 2b
THFN  Parameter: 13.91
sN Parameter: 0.64
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
DOI: 10.1002/anie.201202327
image of molecule

anion of 2-nitro-1-phenylethan-1-one (in DMSO)
DMSON  Parameter: 13.91
sN Parameter: 0.76
***Chem. Eur. J. 2015, 21, 875-884
DOI: 10.1002/chem.201404500
image of molecule

(E)-1-styrylpyrrolidine (in MeCN)
MeCNN  Parameter: 13.87
sN Parameter: 0.76
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

(E)-beta-(N-piperidino)styrene (in MeCN)
MeCNN  Parameter: 13.84
sN Parameter: 0.73
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

anion of diethyl 2-(acetyl)malonate (in DMSO)
DMSON  Parameter: 13.83
sN Parameter: 0.84
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
DMSON  Parameter: 13.79
sN Parameter: 0.86
***Chem. Eur. J. 2014, 20, 11069-11077
DOI: 10.1002/chem.201403161
image of molecule

(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)
DMSON  Parameter: 13.78
sN Parameter: 0.72
***J. Am. Chem. Soc. 2010, 132, 17894-17900
DOI: 10.1021/ja1084749
image of molecule

anion of acetylacetone (in water)
waterN  Parameter: 13.73
sN Parameter: 0.64
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

anion of diethyl 2-(benzoyl)malonate (in DMSO)
DMSON  Parameter: 13.63
sN Parameter: 0.80
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

anion of (4-nitrophenyl)nitromethane (in water)
waterN  Parameter: 13.58
sN Parameter: 0.52
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

anion of p-tolylnitromethane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.58
sN Parameter: 0.64
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

1-(N-morpholino)cyclopentene
dichloromethaneN  Parameter: 13.41
sN Parameter: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

anion of nitroethane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.41
sN Parameter: 0.67
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

1-(N-piperidino)cyclohexene
dichloromethaneN  Parameter: 13.36
sN Parameter: 0.81
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

anion of (4-cyanophenyl)nitromethane (in water)
waterN  Parameter: 13.23
sN Parameter: 0.52
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

anion of p-tolylnitromethane (in water)
waterN  Parameter: 13.09
sN Parameter: 0.50
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

Ph3P=C(CH3)-CO2Et
dichloromethaneN  Parameter: 13.09
sN Parameter: 0.73
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
image of molecule

1-(phenylmethylamino)cyclopentene
dichloromethaneN  Parameter: 12.90
sN Parameter: 0.79
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

Ph3P=CH-CO2Et
dichloromethaneN  Parameter: 12.79
sN Parameter: 0.77
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
image of molecule

Desoxy Breslow intermediate 2c'
THFN  Parameter: 12.75
sN Parameter: 0.71
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
DOI: 10.1002/anie.201202327
image of molecule

5-(trimethylsiloxy)-2,3-dihydrofuran
dichloromethaneN  Parameter: 12.56
sN Parameter: 0.70
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate
MeCNN  Parameter: 12.55
sN Parameter: 0.92
***Chem. Sci. 2012, 3, 878-882
DOI: 10.1039/c2sc00883a
image of molecule

1-(1-cyclohexenyl)-4-methylpiperazine
dichloromethaneN  Parameter: 12.51
sN Parameter: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

anion of phenylnitromethane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 12.51
sN Parameter: 0.67
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

anion of 5-(p-anisyl) Meldrum's acid (in DMSO)
DMSON  Parameter: 12.35
sN Parameter: 0.90
**Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)
MeCNN  Parameter: 12.34
sN Parameter: 0.72
***J. Am. Chem. Soc. 2013, 135, 6579-6587
DOI: 10.1021/ja401106x
image of molecule

Ph3P=CH-CN
dichloromethaneN  Parameter: 12.29
sN Parameter: 0.75
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
image of molecule

(Z)-1-(N-morpholino)propene
dichloromethaneN  Parameter: 12.26
sN Parameter: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

(E)-1-styrylpyrrolidine (in CH2Cl2)
dichloromethaneN  Parameter: 12.26
sN Parameter: 0.93
***J. Am. Chem. Soc. 2014, 136, 14263-14269
DOI: 10.1021/ja508065e
image of molecule

Ph3P=CH-CO2Et (in DMSO)
DMSON  Parameter: 12.21
sN Parameter: 0.62
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
image of molecule

anion of 2-nitropropane (in 91M9AN)
MeOH-MeCN mixN  Parameter: 12.20
sN Parameter: 0.71
***Eur. J. Org. Chem. 2006, , 2530-2537
DOI: 10.1002/ejoc.200500769
image of molecule

(E)-1-(N-morpholino)propene
dichloromethaneN  Parameter: 12.06
sN Parameter: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

anion of Meldrum's acid (in water)
waterN  Parameter: 12.06
sN Parameter: 0.66
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

anion of nitromethane (in water)
waterN  Parameter: 12.06
sN Parameter: 0.53
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

anion of phenylnitromethane (in H2O)
waterN  Parameter: 12.05
sN Parameter: 0.53
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

1-methyl-4-(N-morpholino)tetrahydropyridine
dichloromethaneN  Parameter: 12.03
sN Parameter: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
DMSON  Parameter: 12.02
sN Parameter: 1.17
***Chem. Eur. J. 2014, 20, 11069-11077
DOI: 10.1002/chem.201403161
image of molecule

(E)-1-(2-(4-methoxyphenyl)-1-phenylvinyl)pyrrolidine (in MeCN)
MeCNN  Parameter: 11.99
sN Parameter: 0.84
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

(4-Br-C6H4)-(CO)-CH=SMe2
dichloromethaneN  Parameter: 11.95
sN Parameter: 0.76
***Angew. Chem. Int. Ed. 2009, 48, 5034-5037
DOI: 10.1002/anie.200900933
image of molecule

lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)neopentylglycolborate
MeCNN  Parameter: 11.85
sN Parameter: 0.72
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

anion of dimedone (in water)
waterN  Parameter: 11.77
sN Parameter: 0.63
***J. Am. Chem. Soc. 2003, 125, 12980-12986
DOI: 10.1021/ja036838e
image of molecule

(E)-1-styryl-2-(triphenylsilyl)pyrrolidine (in CH2Cl2)
dichloromethaneN  Parameter: 11.77
sN Parameter: 0.98
***J. Am. Chem. Soc. 2014, 136, 14263-14269
DOI: 10.1021/ja508065e
image of molecule

(E)-1-(1,2-diphenylvinyl)pyrrolidine (in MeCN)
MeCNN  Parameter: 11.66
sN Parameter: 0.82
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

(E)-4-styrylmorpholine
MeCNN  Parameter: 11.66
sN Parameter: 0.83
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

3-ethyl-2,4-dimethylpyrrole
MeCNN  Parameter: 11.63
sN Parameter: 0.95
***Eur. J. Org. Chem. 2008, , 2369-2374
DOI: 10.1002/ejoc.200800092
image of molecule

alpha-(N-piperidino)styrene (in MeCN)
MeCNN  Parameter: 11.60
sN Parameter: 0.80
*Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

anion of 5-phenyl Meldrum's acid (in DMSO)
DMSON  Parameter: 11.54
sN Parameter: 0.95
***Eur. J. Org. Chem. 2016, , 1841-1848
DOI: 10.1002/ejoc.201600107
image of molecule

4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran
dichloromethaneN  Parameter: 11.50
sN Parameter: 0.91
***Eur. J. Org. Chem. 2004, , 2791-2796
DOI: 10.1002/ejoc.200400134
image of molecule

Desoxy Breslow intermediate 2b'
THFN  Parameter: 11.42
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
DOI: 10.1002/anie.201202327
image of molecule

1-(N-morpholino)cyclohexene
dichloromethaneN  Parameter: 11.40
sN Parameter: 0.83
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)
MeCNN  Parameter: 11.29
sN Parameter: 0.76
***Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

5-(triphenylsiloxy)-2,3-dihydrofuran
dichloromethaneN  Parameter: 11.28
sN Parameter: 0.91
***Eur. J. Org. Chem. 2005, , 1760-1764
DOI: 10.1002/ejoc.200400706
image of molecule

anion of nitroethane (in water)
waterN  Parameter: 11.25
sN Parameter: 0.52
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate
MeCNN  Parameter: 11.23
sN Parameter: 0.77
***Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 11.20
sN Parameter: 0.64
*J. Am. Chem. Soc. 2017, 139, 15324-15327
DOI: 10.1021/jacs.7b10240
image of molecule

lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 11.00
sN Parameter: 0.57
***J. Am. Chem. Soc. 2022, 144, 16118-16130
DOI: 10.1021/jacs.2c06493
image of molecule

lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 10.97
sN Parameter: 0.63
**Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

(E)-beta-(N-morpholino)styrene
dichloromethaneN  Parameter: 10.76
sN Parameter: 0.87
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

1-(phenylmethylamino)cyclohexene
dichloromethaneN  Parameter: 10.73
sN Parameter: 0.81
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

anion of 2-nitropropane (in water)
waterN  Parameter: 10.69
sN Parameter: 0.56
***J. Org. Chem. 2004, 69, 7565-7576
DOI: 10.1021/jo048773j
image of molecule

2,4-dimethylpyrrole
MeCNN  Parameter: 10.67
sN Parameter: 0.91
***Eur. J. Org. Chem. 2008, , 2369-2374
DOI: 10.1002/ejoc.200800092
image of molecule

(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN)
MeCNN  Parameter: 10.63
sN Parameter: 0.84
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

2-(trimethylsiloxy)-5,6-dihydro-4H-pyran
dichloromethaneN  Parameter: 10.61
sN Parameter: 0.86
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine
MeCNN  Parameter: 10.56
sN Parameter: 1.01
***Angew. Chem. Int. Ed. 2012, 51, 5739-5742
DOI: 10.1002/anie.201201240
image of molecule

2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)
MeCNN  Parameter: 10.52
sN Parameter: 0.78
***J. Am. Chem. Soc. 2013, 135, 6579-6587
DOI: 10.1021/ja401106x
image of molecule

diazomethane
dichloromethaneN  Parameter: 10.48
sN Parameter: 0.78
***Chem. Eur. J. 2003, 9, 4068-4076
DOI: 10.1002/chem.200304913
image of molecule

MeO-Breslow 1b
THFN  Parameter: 10.45
sN Parameter: 0.81
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
DOI: 10.1002/anie.201204524
image of molecule

(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN)
MeCNN  Parameter: 10.42
sN Parameter: 0.82
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

1,1-bis(trimethylsiloxy)propene
dichloromethaneN  Parameter: 10.38
sN Parameter: 0.87
****Eur. J. Org. Chem. 2004, , 2791-2796
DOI: 10.1002/ejoc.200400134
image of molecule

1-butoxy-1-(t-butyl-dimethylsiloxy)ethene
dichloromethaneN  Parameter: 10.32
sN Parameter: 0.79
****Eur. J. Org. Chem. 2004, , 2791-2796
DOI: 10.1002/ejoc.200400134
image of molecule

alpha-(N-morpholino)styrene (in MeCN)
MeCNN  Parameter: 10.30
sN Parameter: 0.80
*Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

Ph3P=CH-C(O)Me (in MeCN)
MeCNN  Parameter: 10.27
sN Parameter: 0.83
***J. Am. Chem. Soc. 2016, 138, 11272-11281
DOI: 10.1021/jacs.6b06264
image of molecule

1-butoxy-1-(trimethylsiloxy)ethene
dichloromethaneN  Parameter: 10.21
sN Parameter: 0.82
****Eur. J. Org. Chem. 2004, , 2791-2796
DOI: 10.1002/ejoc.200400134
image of molecule

(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2)
dichloromethaneN  Parameter: 10.19
sN Parameter: 1.06
***J. Am. Chem. Soc. 2014, 136, 14263-14269
DOI: 10.1021/ja508065e
image of molecule

lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate
MeCNN  Parameter: 10.13
sN Parameter: 0.91
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

morpholinoisobutylene
dichloromethaneN  Parameter: 10.04
sN Parameter: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

alpha-(N-morpholino)styrene
dichloromethaneN  Parameter: 9.96
sN Parameter: 0.79
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN)
MeCNN  Parameter: 9.94
sN Parameter: 0.86
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

1,1-diethoxyethene
dichloromethaneN  Parameter: 9.81
sN Parameter: 0.81
***Eur. J. Org. Chem. 2004, , 2791-2796
DOI: 10.1002/ejoc.200400134
image of molecule

(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)
MeCNN  Parameter: 9.64
sN Parameter: 0.70
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

potassium trifluoro(1-methyl-1H-indol-2-yl)borate
MeCNN  Parameter: 9.55
sN Parameter: 1.16
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

Ph3P=CH-COPh
dichloromethaneN  Parameter: 9.54
sN Parameter: 0.97
***J. Am. Chem. Soc. 2009, 131, 704-714
DOI: 10.1021/ja8056216
image of molecule

lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 9.49
sN Parameter: 0.82
***J. Am. Chem. Soc. 2017, 139, 15324-15327
DOI: 10.1021/jacs.7b10240
image of molecule

ethyl (E)-3-(dimethylamino)acrylate
dichloromethaneN  Parameter: 9.43
sN Parameter: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

phenyldiazomethane
dichloromethaneN  Parameter: 9.35
sN Parameter: 0.83
***Chem. Eur. J. 2003, 9, 4068-4076
DOI: 10.1002/chem.200304913
image of molecule

2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
MeCNN  Parameter: 9.25
sN Parameter: 0.84
***Chem. Commun. 2023, 59, 8091-8084
DOI: 10.1039/d3cc01912h
image of molecule

(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
MeCNN  Parameter: 9.23
sN Parameter: 0.74
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)
MeCNN  Parameter: 9.11
sN Parameter: 0.88
***J. Am. Chem. Soc. 2013, 135, 6579-6587
DOI: 10.1021/ja401106x
image of molecule

tetrakis(5-methyl-furan-2-yl)borate
MeCNN  Parameter: 9.09
sN Parameter: 1.12
***Chem. Sci. 2012, 3, 878-882
DOI: 10.1039/c2sc00883a
image of molecule

Ph3P=CH-CHO (in MeCN)
MeCNN  Parameter: 9.09
sN Parameter: 0.74
***J. Am. Chem. Soc. 2016, 138, 11272-11281
DOI: 10.1021/jacs.6b06264
image of molecule

1-methoxy-2-methyl-1-(trimethylsiloxy)propene
dichloromethaneN  Parameter: 9.00
sN Parameter: 0.98
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

(trimethylsilyl)diazomethane
dichloromethaneN  Parameter: 8.97
sN Parameter: 0.75
***Chem. Eur. J. 2003, 9, 4068-4076
DOI: 10.1002/chem.200304913
image of molecule

lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 8.92
sN Parameter: 0.70
**Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

(p-bromophenyl)diazomethane
dichloromethaneN  Parameter: 8.87
sN Parameter: 0.82
***J. Am. Chem. Soc. 2018, 140, 16758-16772
DOI: 10.1021/jacs.8b09995
image of molecule

(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN)
MeCNN  Parameter: 8.78
sN Parameter: 0.83
***Chem. Eur. J. 2018, 24, 5901-5910
DOI: 10.1002/chem.201705962
image of molecule

potassium trifluoro(1-methyl-1H-indol-5-yl)borate
MeCNN  Parameter: 8.77
sN Parameter: 1.09
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 8.71
sN Parameter: 0.80
***J. Am. Chem. Soc. 2017, 139, 15324-15327
DOI: 10.1021/jacs.7b10240
image of molecule

1,2,5-trimethylpyrrole
MeCNN  Parameter: 8.69
sN Parameter: 1.07
***Eur. J. Org. Chem. 2008, , 2369-2374
DOI: 10.1002/ejoc.200800092
image of molecule

Danishefskys diene
dichloromethaneN  Parameter: 8.57
sN Parameter: 0.84
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 8.56
sN Parameter: 0.76
***Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

ethyl (E)-3-(N-morpholino)acrylate
dichloromethaneN  Parameter: 8.52
sN Parameter: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)
dichloromethaneN  Parameter: 8.45
sN Parameter: 0.83
***Helv. Chim. Acta 2005, 88, 1754-1768
DOI: 10.1002/hlca.200590137
image of molecule

(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)
MeCNN  Parameter: 8.30
sN Parameter: 0.84
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

1-phenoxy-1-(trimethylsiloxy)ethene
dichloromethaneN  Parameter: 8.23
sN Parameter: 0.81
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran
dichloromethaneN  Parameter: 8.16
sN Parameter: 0.67
***Eur. J. Org. Chem. 2005, , 1760-1764
DOI: 10.1002/ejoc.200400706
image of molecule

lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate
MeCNN  Parameter: 8.13
sN Parameter: 0.85
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)
dichloromethaneN  Parameter: 8.13
sN Parameter: 0.97
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)
MeCNN  Parameter: 8.12
sN Parameter: 0.88
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate
MeCNN  Parameter: 8.02
sN Parameter: 0.89
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

2,5-dimethylpyrrole
MeCNN  Parameter: 8.01
sN Parameter: 0.96
***Eur. J. Org. Chem. 2008, , 2369-2374
DOI: 10.1002/ejoc.200800092
image of molecule

(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)
dichloromethaneN  Parameter: 7.99
sN Parameter: 0.98
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2)
dichloromethaneN  Parameter: 7.98
sN Parameter: 0.71
***J. Am. Chem. Soc. 2016, 138, 10304-10313
DOI: 10.1021/jacs.6b05768
image of molecule

(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one
MeCNN  Parameter: 7.92
sN Parameter: 1.07
***Angew. Chem. Int. Ed. 2012, 51, 5739-5742
DOI: 10.1002/anie.201201240
image of molecule

(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylbut-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)
MeCNN  Parameter: 7.92
sN Parameter: 0.73
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

N-methylenepyrrolidin-1-amine (in CH2Cl2)
dichloromethaneN  Parameter: 7.84
sN Parameter: 0.89
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
DOI: 10.1002/anie.201305092
image of molecule

6-(julolidin-9-yl)fulvene
MeCNN  Parameter: 7.79
sN Parameter: 1.06
***Eur. J. Org. Chem. 2009, , 1202-1206
DOI: 10.1002/ejoc.200801099
image of molecule

(E)-13-(ethylthio)-6-styryl-6,12-diazadispiro[4.1.47.25]tridec-12-ene (in MeCN)
MeCNN  Parameter: 7.79
sN Parameter: 0.87
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
MeCNN  Parameter: 7.74
sN Parameter: 0.87
***Chem. Commun. 2023, 59, 8091-8084
DOI: 10.1039/d3cc01912h
image of molecule

lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 7.72
sN Parameter: 0.75
*Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 7.68
sN Parameter: 0.78
***Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

lithium bis(5-methylthiophen-2-yl)pinacolborate
MeCNN  Parameter: 7.67
sN Parameter: 0.87
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

(5-methyl-furan-2-yl) trifluoroborate
MeCNN  Parameter: 7.66
sN Parameter: 1.04
***Chem. Sci. 2012, 3, 878-882
DOI: 10.1039/c2sc00883a
image of molecule

(p-cyanophenyl)diazomethane
dichloromethaneN  Parameter: 7.66
sN Parameter: 0.80
***J. Am. Chem. Soc. 2018, 140, 16758-16772
DOI: 10.1021/jacs.8b09995
image of molecule

lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate
MeCNN  Parameter: 7.51
sN Parameter: 0.87
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

(2-methylallyl)tributylstannane
dichloromethaneN  Parameter: 7.48
sN Parameter: 0.89
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 7.46
sN Parameter: 0.76
**Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

potassium trifluoro(3-methoxy-thiophen-2-yl)borate
MeCNN  Parameter: 7.32
sN Parameter: 0.90
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

3-(trimethylsiloxy)-1H-indene (in MeCN)
MeCNN  Parameter: 7.32
sN Parameter: 0.82
***Synthesis 2019, 51, 1157-1170
DOI: 10.1055/s-0037-1611634
image of molecule

5-methoxy-2-methylindole
MeCNN  Parameter: 7.26
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

lithium (5-methylthiophen-2-yl)(phenyl)pinacolborate
MeCNN  Parameter: 7.24
sN Parameter: 0.83
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

2-(trimethylsiloxy)furan
dichloromethaneN  Parameter: 7.22
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

5-amino-indole
MeCNN  Parameter: 7.22
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

2,5-dimethylindole
MeCNN  Parameter: 7.22
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one
MeCNN  Parameter: 7.20
sN Parameter: 1.14
***Angew. Chem. Int. Ed. 2012, 51, 5739-5742
DOI: 10.1002/anie.201201240
image of molecule

(p-nitrophenyl)diazomethane
dichloromethaneN  Parameter: 7.17
sN Parameter: 0.83
***J. Am. Chem. Soc. 2018, 140, 16758-16772
DOI: 10.1021/jacs.8b09995
image of molecule

lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 7.15
sN Parameter: 0.77
***Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate
MeCNN  Parameter: 7.10
sN Parameter: 1.18
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidin-4-one (in MeCN)
MeCNN  Parameter: 7.10
sN Parameter: 0.82
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

N-(1-(4-methoxyphenyl)vinyl)acetamide
MeCNN  Parameter: 7.06
sN Parameter: 0.85
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

N-(cyclopent-1-en-1-yl)acetamide
MeCNN  Parameter: 7.06
sN Parameter: 0.87
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in CH2Cl2)
dichloromethaneN  Parameter: 7.06
sN Parameter: 1.11
***Chem. Commun. 2023, 59, 8091-8084
DOI: 10.1039/d3cc01912h
image of molecule

1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
dichloromethaneN  Parameter: 6.98
sN Parameter: 0.85
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
DOI: 10.1002/anie.201305092
image of molecule

lithium (5-methylthiophen-2-yl)(4-methylphenyl)pinacolborate
MeCNN  Parameter: 6.98
sN Parameter: 0.93
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

2-methylindole
MeCNN  Parameter: 6.91
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

Dimethyl bis(indenyl)zirconium(IV)
dichloromethaneN  Parameter: 6.89
sN Parameter: 1.00
*Chem. Eur. J. 2016, 22, 11196-11200
DOI: 10.1002/chem.201602452
image of molecule

potassium trifluoro(furan-3-yl)borate
MeCNN  Parameter: 6.83
sN Parameter: 0.93
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

(allyl)dicarbonyl(cyclopentadienyl)iron(II)
dichloromethaneN  Parameter: 6.78
sN Parameter: 0.95
***Helv. Chim. Acta 2005, 88, 1754-1768
DOI: 10.1002/hlca.200590137
image of molecule

1-(trimethylsiloxy)cyclooctene
dichloromethaneN  Parameter: 6.77
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate
MeCNN  Parameter: 6.77
sN Parameter: 0.88
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

6-(4-dimethylamino-phenyl)fulvene
MeCNN  Parameter: 6.72
sN Parameter: 0.87
***Eur. J. Org. Chem. 2009, , 1202-1206
DOI: 10.1002/ejoc.200801099
image of molecule

(1H-inden-1-yl)trimethylstannane (in CH2Cl2)
dichloromethaneN  Parameter: 6.68
sN Parameter: 0.81
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
DOI: 10.1002/anie.201501385
image of molecule

azulene
MeCNN  Parameter: 6.66
sN Parameter: 1.02
***Eur. J. Org. Chem. 2009, , 1202-1206
DOI: 10.1002/ejoc.200801099
image of molecule

lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 6.63
sN Parameter: 0.75
*Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

1-(trimethylsiloxy)cycloheptene
dichloromethaneN  Parameter: 6.62
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

1-(trimethylsiloxy)cyclopentene
dichloromethaneN  Parameter: 6.57
sN Parameter: 0.93
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

N-(1-(p-tolyl)vinyl)acetamide
MeCNN  Parameter: 6.57
sN Parameter: 0.91
**Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

1,2-dimethylindole
dichloromethaneN  Parameter: 6.54
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)catecholglycolborate
MeCNN  Parameter: 6.50
sN Parameter: 0.77
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN)
MeCNN  Parameter: 6.49
sN Parameter: 0.83
***Chem. Eur. J. 2024, 30, e202302764
DOI: 10.1002/chem.202302764
image of molecule

potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate
MeCNN  Parameter: 6.46
sN Parameter: 0.96
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

5-hydroxy-indole
MeCNN  Parameter: 6.44
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

1-(trimethylsiloxy)cyclopentene (in MeCN)
MeCNN  Parameter: 6.43
sN Parameter: 0.89
***Chem. Asian J. 2012, 7, 1401-1407
DOI: 10.1002/asia.201101046
image of molecule

(5-methyl-furan-2-yl) MDA boronate
MeCNN  Parameter: 6.38
sN Parameter: 0.86
***Chem. Sci. 2012, 3, 878-882
DOI: 10.1039/c2sc00883a
image of molecule

lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)
MeCNN  Parameter: 6.30
sN Parameter: 0.78
**Org. Lett. 2015, 17, 2614-2617
DOI: 10.1021/acs.orglett.5b00918
image of molecule

N-(1-(naphthalen-2-yl)vinyl)acetamide
MeCNN  Parameter: 6.28
sN Parameter: 0.95
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate
MeCNN  Parameter: 6.24
sN Parameter: 1.00
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

1-phenyl-1-(trimethylsiloxy)ethene
dichloromethaneN  Parameter: 6.22
sN Parameter: 0.96
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

5-methoxy-indole
dichloromethaneN  Parameter: 6.22
sN Parameter: 1.12
***J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

benzyl (1-phenylvinyl)carbamate
MeCNN  Parameter: 6.21
sN Parameter: 0.87
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

Dimedone iodonium ylide (in CH2Cl2)
dichloromethaneN  Parameter: 6.18
sN Parameter: 0.81
***J. Am. Chem. Soc. 2016, 138, 10304-10313
DOI: 10.1021/jacs.6b05768
image of molecule

5-chloro-2-methylindole
MeCNN  Parameter: 6.08
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

2-(tris(trimethylsilyl)siloxy)propene
dichloromethaneN  Parameter: 6.04
sN Parameter: 0.82
***Org. Lett. 2010, 12, 5206-5209
DOI: 10.1021/ol102220e
image of molecule

5-methyl-indole
MeCNN  Parameter: 6.00
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

potassium trifluoro(furan-2-yl)borate
MeCNN  Parameter: 5.99
sN Parameter: 0.79
**J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

N-methylpyrrole
dichloromethaneN  Parameter: 5.85
sN Parameter: 1.03
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one
MeCNN  Parameter: 5.80
sN Parameter: 0.87
***Angew. Chem. Int. Ed. 2012, 51, 5739-5742
DOI: 10.1002/anie.201201240
image of molecule

1-(triphenylsiloxy)cyclopentene
dichloromethaneN  Parameter: 5.76
sN Parameter: 1.02
****Eur. J. Org. Chem. 2005, , 1760-1764
DOI: 10.1002/ejoc.200400706
image of molecule

N-methylindole
dichloromethaneN  Parameter: 5.75
sN Parameter: 1.23
***J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

N-(1-phenylvinyl)acetamide
MeCNN  Parameter: 5.73
sN Parameter: 0.97
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

N-(cyclohex-1-en-1-yl)acetamide
MeCNN  Parameter: 5.64
sN Parameter: 0.79
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

2-diazoindan-1-one
dichloromethaneN  Parameter: 5.61
sN Parameter: 0.65
***Eur. J. Org. Chem. 2023, 26, e202300005
DOI: 10.1002/ejoc.202300005
image of molecule

N-(1-(4-chlorophenyl)vinyl)acetamide
MeCNN  Parameter: 5.60
sN Parameter: 1.00
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

Z-3-(trimethylsiloxy)pent-2-ene
dichloromethaneN  Parameter: 5.58
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-(tert.butyldimethylsiloxy)propene
dichloromethaneN  Parameter: 5.58
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

Indole
dichloromethaneN  Parameter: 5.55
sN Parameter: 1.09
***J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate
MeCNN  Parameter: 5.53
sN Parameter: 1.00
*Angew. Chem. Int. Ed. 2015, 54, 2780-2783
DOI: 10.1002/anie.201410562
image of molecule

(Cp*)2Zr(Me)2 - Dimethyl-bis(pentamethylcyclopentadienyl)zirconium
dichloromethaneN  Parameter: 5.49
sN Parameter: 1.06
***Chem. Eur. J. 2016, 22, 11196-11200
DOI: 10.1002/chem.201602452
image of molecule

tert-butyl isocyanide
dichloromethaneN  Parameter: 5.47
sN Parameter: 0.77
***Angew. Chem. Int. Ed. 2007, 46, 3563-3566
DOI: 10.1002/anie.200605205
image of molecule

allyltributylstannane
dichloromethaneN  Parameter: 5.46
sN Parameter: 0.89
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

N-(1-phenylvinyl)benzamide
MeCNN  Parameter: 5.44
sN Parameter: 1.00
*Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

2-(trimethylsiloxy)propene
dichloromethaneN  Parameter: 5.41
sN Parameter: 0.91
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

4-methoxy-indole
MeCNN  Parameter: 5.41
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

3-methyl-2-(trimethylsiloxy)but-1-ene
dichloromethaneN  Parameter: 5.41
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-(triisopropylsiloxy)propene
dichloromethaneN  Parameter: 5.38
sN Parameter: 0.85
**J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2-phenyl-allyltrimethylsilane
dichloromethaneN  Parameter: 5.38
sN Parameter: 0.89
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

diphenyldiazomethane
dichloromethaneN  Parameter: 5.29
sN Parameter: 0.92
***Chem. Eur. J. 2003, 9, 4068-4076
DOI: 10.1002/chem.200304913
image of molecule

potassium allyltrifluoroborate (in MeCN)
MeCNN  Parameter: 5.29
sN Parameter: 0.87
**J. Am. Chem. Soc. 2017, 139, 15324-15327
DOI: 10.1021/jacs.7b10240
image of molecule

1-(trimethylsiloxy)cyclohexene
dichloromethaneN  Parameter: 5.21
sN Parameter: 1.00
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

Dimethyl 1,1'-isopropylidenezirconocene
dichloromethaneN  Parameter: 5.20
sN Parameter: 1.00
*Chem. Eur. J. 2016, 22, 11196-11200
DOI: 10.1002/chem.201602452
image of molecule

(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN)
MeCNN  Parameter: 5.18
sN Parameter: 0.94
***Synthesis 2019, 51, 1157-1170
DOI: 10.1055/s-0037-1611634
image of molecule

N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide
dichloromethaneN  Parameter: 5.16
sN Parameter: 0.85
***Angew. Chem. Int. Ed. 2014, 53, 4968-4971
DOI: 10.1002/anie.201402055
image of molecule

(2-methylallyl)triphenylstannane
dichloromethaneN  Parameter: 5.13
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

Cp2Zr(CH2Ph)2 - Dibenzylzirconocene
dichloromethaneN  Parameter: 5.10
sN Parameter: 1.03
***Chem. Eur. J. 2016, 22, 11196-11200
DOI: 10.1002/chem.201602452
image of molecule

1-(tris(trimethylsilyl)siloxy)cyclohexene
dichloromethaneN  Parameter: 5.07
sN Parameter: 0.91
***Org. Lett. 2010, 12, 5206-5209
DOI: 10.1021/ol102220e
image of molecule

1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN)
MeCNN  Parameter: 5.06
sN Parameter: 0.91
***Synthesis 2019, 51, 1157-1170
DOI: 10.1055/s-0037-1611634
image of molecule

N-vinylcarbazole
dichloromethaneN  Parameter: 5.02
sN Parameter: 0.94
**Macromolecules 2002, 35, 5454-5458
DOI: 10.1021/ma020306l
image of molecule

ethyl diazoacetate
dichloromethaneN  Parameter: 4.91
sN Parameter: 0.95
***Chem. Eur. J. 2003, 9, 4068-4076
DOI: 10.1002/chem.200304913
image of molecule

N-(3,4-dihydronaphthalen-1-yl)acetamide
MeCNN  Parameter: 4.91
sN Parameter: 0.87
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

benzyl isocyanide
dichloromethaneN  Parameter: 4.90
sN Parameter: 0.74
***Angew. Chem. Int. Ed. 2007, 46, 3563-3566
DOI: 10.1002/anie.200605205
image of molecule

diazocyclopentadiene (in CH2Cl2)
dichloromethaneN  Parameter: 4.84
sN Parameter: 1.06
***Synthesis 2023, 55, 354-358
DOI: 10.1055/s-0041-1737327
image of molecule

2-(trimethylsiloxy)buta-1,3-diene
dichloromethaneN  Parameter: 4.83
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(bis(trimethylsiloxy)amino)styrene
dichloromethaneN  Parameter: 4.80
sN Parameter: 0.86
*J. Org. Chem. 2001, 66, 3196-3200
DOI: 10.1021/jo0015927
image of molecule

2-(bis(trimethylsiloxy)amino)propene
dichloromethaneN  Parameter: 4.76
sN Parameter: 0.86
***J. Org. Chem. 2001, 66, 3196-3200
DOI: 10.1021/jo0015927
image of molecule

prenyl-tributylstannane
dichloromethaneN  Parameter: 4.74
sN Parameter: 1.15
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

methyl diazoacetate
dichloromethaneN  Parameter: 4.68
sN Parameter: 0.94
***J. Am. Chem. Soc. 2023, 145, 7416-7434
DOI: 10.1021/jacs.2c13872
image of molecule

(2-methylallyl)triphenylgermane
dichloromethaneN  Parameter: 4.67
sN Parameter: 0.81
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2)
dichloromethaneN  Parameter: 4.67
sN Parameter: 0.92
***J. Am. Chem. Soc. 2016, 138, 10304-10313
DOI: 10.1021/jacs.6b05768
image of molecule

pyrrole
dichloromethaneN  Parameter: 4.63
sN Parameter: 1.00
*Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

(2-methylallyl)tris(trimethylsilyl)silane
dichloromethaneN  Parameter: 4.63
sN Parameter: 0.87
***Org. Lett. 2010, 12, 5206-5209
DOI: 10.1021/ol102220e
image of molecule

N-(3,3-dimethylbut-1-en-2-yl)acetamide
MeCNN  Parameter: 4.61
sN Parameter: 0.98
***Chem. Eur. J. 2012, 18, 5732-5740
DOI: 10.1002/chem.201103519
image of molecule

1-(trimethylsiloxy)buta-1,3-diene
dichloromethaneN  Parameter: 4.60
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2,6-dimethylphenyl isocyanide
dichloromethaneN  Parameter: 4.59
sN Parameter: 0.87
***Angew. Chem. Int. Ed. 2007, 46, 3563-3566
DOI: 10.1002/anie.200605205
image of molecule

1,2-bis(trimethylsiloxy)cyclohexene
dichloromethaneN  Parameter: 4.46
sN Parameter: 1.15
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-(triphenylsiloxy)propene
dichloromethaneN  Parameter: 4.46
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

5-chloro-indole
MeCNN  Parameter: 4.42
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

(2-methylallyl)trimethylsilane
dichloromethaneN  Parameter: 4.41
sN Parameter: 0.96
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide
dichloromethaneN  Parameter: 4.40
sN Parameter: 0.86
***Angew. Chem. Int. Ed. 2014, 53, 4968-4971
DOI: 10.1002/anie.201402055
image of molecule

5-bromo-indole
MeCNN  Parameter: 4.38
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

Cp2Ti(CH2Ph)2 - Dibenzyltitanocene
dichloromethaneN  Parameter: 4.38
sN Parameter: 1.00
*Chem. Eur. J. 2016, 22, 11196-11200
DOI: 10.1002/chem.201602452
image of molecule

2,3-dihydrofuran
dichloromethaneN  Parameter: 4.37
sN Parameter: 0.90
****Eur. J. Org. Chem. 2005, , 1760-1764
DOI: 10.1002/ejoc.200400706
image of molecule

Meldrum's acid iodonium ylide (in CH2Cl2)
dichloromethaneN  Parameter: 4.36
sN Parameter: 1.06
***J. Am. Chem. Soc. 2016, 138, 10304-10313
DOI: 10.1021/jacs.6b05768
image of molecule

Cp2Zr(Me)2 - Dimethylzirconocene
dichloromethaneN  Parameter: 4.35
sN Parameter: 1.09
***Chem. Eur. J. 2016, 22, 11196-11200
DOI: 10.1002/chem.201602452
image of molecule

2-(bis(tert-butyldimethylsiloxy)amino)propene
dichloromethaneN  Parameter: 4.23
sN Parameter: 0.93
***J. Org. Chem. 2001, 66, 3196-3200
DOI: 10.1021/jo0015927
image of molecule

isobutylenyl-ethylether
dichloromethaneN  Parameter: 4.23
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(2-methylallyl)triphenylsilane
dichloromethaneN  Parameter: 4.17
sN Parameter: 0.79
**J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate
MeCNN  Parameter: 4.06
sN Parameter: 0.79
**J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

(tris(trimethylsilyl)siloxy)ethene
dichloromethaneN  Parameter: 4.01
sN Parameter: 0.83
***Org. Lett. 2010, 12, 5206-5209
DOI: 10.1021/ol102220e
image of molecule

1H-indole-5-carboxylic acid
MeCNN  Parameter: 3.97
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

diazoacetone
dichloromethaneN  Parameter: 3.96
sN Parameter: 0.91
***Chem. Eur. J. 2003, 9, 4068-4076
DOI: 10.1002/chem.200304913
image of molecule

2-methyl-1-(trimethylsiloxy)propen
dichloromethaneN  Parameter: 3.94
sN Parameter: 1.00
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

6,6-dimethylfulvene
MeCNN  Parameter: 3.93
sN Parameter: 0.88
***Eur. J. Org. Chem. 2009, , 1202-1206
DOI: 10.1002/ejoc.200801099
image of molecule

ethyl-vinylether
dichloromethaneN  Parameter: 3.92
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(Z)-1-(triisopropylsiloxy)propen
dichloromethaneN  Parameter: 3.87
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

7-azaindole
MeCNN  Parameter: 3.87
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide
dichloromethaneN  Parameter: 3.85
sN Parameter: 0.84
***Angew. Chem. Int. Ed. 2014, 53, 4968-4971
DOI: 10.1002/anie.201402055
image of molecule

4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester
dichloromethaneN  Parameter: 3.84
sN Parameter: 0.87
***J. Org. Chem. 2001, 66, 3196-3200
DOI: 10.1021/jo0015927
image of molecule

3,3-dimethyl-2-(trimethylsiloxy)buten
dichloromethaneN  Parameter: 3.78
sN Parameter: 0.79
**J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

n-butyl vinyl ether
dichloromethaneN  Parameter: 3.76
sN Parameter: 0.91
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

2-(tributylstannyl)furan
dichloromethaneN  Parameter: 3.63
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-methylfuran
dichloromethaneN  Parameter: 3.61
sN Parameter: 1.11
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

4-cyanophenyl isocyanide
dichloromethaneN  Parameter: 3.57
sN Parameter: 0.72
**Angew. Chem. Int. Ed. 2007, 46, 3563-3566
DOI: 10.1002/anie.200605205
image of molecule

2-diazo-1-tetralone
dichloromethaneN  Parameter: 3.51
sN Parameter: 0.86
***Eur. J. Org. Chem. 2023, 26, e202300005
DOI: 10.1002/ejoc.202300005
image of molecule

p-tosylmethyl isocyanide (TosMIC)
dichloromethaneN  Parameter: 3.50
sN Parameter: 0.76
***Angew. Chem. Int. Ed. 2007, 46, 3563-3566
DOI: 10.1002/anie.200605205
image of molecule

(triisopropylsiloxy)ethene
dichloromethaneN  Parameter: 3.44
sN Parameter: 0.94
**J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2-diazocyclohexanone
dichloromethaneN  Parameter: 3.44
sN Parameter: 0.83
***Eur. J. Org. Chem. 2023, 26, e202300005
DOI: 10.1002/ejoc.202300005
image of molecule

cyclohepta-1,3,5-trienyl-Fe(CO)3
dichloromethaneN  Parameter: 3.42
sN Parameter: 0.94
***J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

methylenecyclooctane
dichloromethaneN  Parameter: 3.16
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

3-diazoindolin-2-one
dichloromethaneN  Parameter: 3.16
sN Parameter: 1.03
***Eur. J. Org. Chem. 2023, 26, e202300005
DOI: 10.1002/ejoc.202300005
image of molecule

(2,3-dimethylbut-2-enyl)triethylsilane
dichloromethaneN  Parameter: 3.15
sN Parameter: 1.15
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

N-(triisopropylsilyl)pyrrole
dichloromethaneN  Parameter: 3.12
sN Parameter: 0.93
***Chem. Eur. J. 2003, 9, 2209-2218
DOI: 10.1002/chem.200204666
image of molecule

1-(phenylethynyl)pyrrolidin-2-one
dichloromethaneN  Parameter: 3.12
sN Parameter: 0.85
*Angew. Chem. Int. Ed. 2014, 53, 4968-4971
DOI: 10.1002/anie.201402055
image of molecule

allyltriphenylstannane
dichloromethaneN  Parameter: 3.09
sN Parameter: 0.90
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

(E)-2-methyl-penta-1,3-diene
dichloromethaneN  Parameter: 3.09
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

3-methoxythiophene
MeCNN  Parameter: 3.06
sN Parameter: 1.19
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN)
MeCNN  Parameter: 3.00
sN Parameter: 0.83
***Synthesis 2019, 51, 1157-1170
DOI: 10.1055/s-0037-1611634
image of molecule

(5-methyl-furan-2-yl) pinacol boronate
MeCNN  Parameter: 2.90
sN Parameter: 0.98
***Chem. Sci. 2012, 3, 878-882
DOI: 10.1039/c2sc00883a
image of molecule

5-cyano-indole
MeCNN  Parameter: 2.83
sN Parameter: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
DOI: 10.1021/jo0614339
image of molecule

methylenecyclopentane
dichloromethaneN  Parameter: 2.82
sN Parameter: 0.90
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

methylenecyclodecane
dichloromethaneN  Parameter: 2.82
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-diazo-1-benzosuberone
dichloromethaneN  Parameter: 2.72
sN Parameter: 0.96
***Eur. J. Org. Chem. 2023, 26, e202300005
DOI: 10.1002/ejoc.202300005
image of molecule

4-methyl-penta-1,3-diene
dichloromethaneN  Parameter: 2.60
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-cyclopropylpropene
dichloromethaneN  Parameter: 2.60
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

methylenecyclononane
dichloromethaneN  Parameter: 2.57
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

1,3-dimethoxybenzene
dichloromethaneN  Parameter: 2.48
sN Parameter: 1.09
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2-(tributylsilyl)furan
dichloromethaneN  Parameter: 2.37
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

alpha-methylstyrene
dichloromethaneN  Parameter: 2.35
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

methylenecycloundecane
dichloromethaneN  Parameter: 2.33
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

cyclopentadiene
dichloromethaneN  Parameter: 2.30
sN Parameter: 1.06
***Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

methylenecycloheptane
dichloromethaneN  Parameter: 2.24
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-(triethylsilyl)furan
dichloromethaneN  Parameter: 2.20
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-(trimethylsilyl)furan
dichloromethaneN  Parameter: 2.16
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allyltrihexylsilane
dichloromethaneN  Parameter: 2.11
sN Parameter: 0.95
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allyltri-n-butylsilane
dichloromethaneN  Parameter: 2.09
sN Parameter: 0.95
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allyltriisopropylsilane
dichloromethaneN  Parameter: 2.04
sN Parameter: 0.95
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

3-(trihexylsilyl)cyclopentene
dichloromethaneN  Parameter: 1.98
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allyltris(trimethylsilyl)silane
dichloromethaneN  Parameter: 1.95
sN Parameter: 0.98
***Org. Lett. 2010, 12, 5206-5209
DOI: 10.1021/ol102220e
image of molecule

(E)-but-2-enyltrimethylsilane
dichloromethaneN  Parameter: 1.94
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allyltriethylsilane
dichloromethaneN  Parameter: 1.93
sN Parameter: 0.95
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(5-methyl-furan-2-yl) MIDA boronate
MeCNN  Parameter: 1.84
sN Parameter: 1.26
**Chem. Sci. 2012, 3, 878-882
DOI: 10.1039/c2sc00883a
image of molecule

allyl-tert.butyl-dimethylsilane
dichloromethaneN  Parameter: 1.80
sN Parameter: 0.95
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

3-(trimethylsilyl)cyclopentene
dichloromethaneN  Parameter: 1.77
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

1-methyl-4-vinyl-benzene
dichloromethaneN  Parameter: 1.70
sN Parameter: 1.06
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

methylenecyclopentadecane
dichloromethaneN  Parameter: 1.69
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(Z)-but-2-enyltrimethylsilane
dichloromethaneN  Parameter: 1.69
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2,6-dimethyl-hepta-1,6-diene
dichloromethaneN  Parameter: 1.69
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allyltrimethylsilane
dichloromethaneN  Parameter: 1.68
sN Parameter: 1.00
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

tert-butyl indole-1-carboxylate
MeCNN  Parameter: 1.68
sN Parameter: 1.26
***J. Am. Chem. Soc. 2013, 135, 6317-6324
DOI: 10.1021/ja4017655
image of molecule

methylenecyclobutane
dichloromethaneN  Parameter: 1.65
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2,7-dimethylocta-1,7-diene
dichloromethaneN  Parameter: 1.58
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-(tributylstannyl)thiophene
dichloromethaneN  Parameter: 1.53
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

methylenecyclododecane
dichloromethaneN  Parameter: 1.52
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(E)-penta-1,3-diene
dichloromethaneN  Parameter: 1.49
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

1-(perfluorophenyl)-1-(trimethylsiloxy)ethene
dichloromethaneN  Parameter: 1.47
sN Parameter: 0.89
***Org. Lett. 2012, 14, 3990-3993
DOI: 10.1021/ol301766w
image of molecule

1-(tris(pentafluorophenyl)siloxy)-cyclopentene
dichloromethaneN  Parameter: 1.38
sN Parameter: 0.93
*Eur. J. Org. Chem. 2005, , 1760-1764
DOI: 10.1002/ejoc.200400706
image of molecule

2-methylthiophene
dichloromethaneN  Parameter: 1.35
sN Parameter: 0.99
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

furan
dichloromethaneN  Parameter: 1.33
sN Parameter: 1.29
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6
dichloromethaneN  Parameter: 1.33
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allyltriphenylgermane
dichloromethaneN  Parameter: 1.20
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

1-methylcyclopentene
dichloromethaneN  Parameter: 1.18
sN Parameter: 1.17
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

(E,E)-hexa-2,4-diene
dichloromethaneN  Parameter: 1.17
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2,3-dimethyl-buta-1,3-diene
dichloromethaneN  Parameter: 1.17
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

methylenecyclohexane
dichloromethaneN  Parameter: 1.16
sN Parameter: 1.04
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

2,5-dimethyl-hexa-1,5-diene
dichloromethaneN  Parameter: 1.14
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-methylpropene (isobutylene)
dichloromethaneN  Parameter: 1.11
sN Parameter: 0.98
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2-methyl-buta-1,3-diene (isoprene)
dichloromethaneN  Parameter: 1.10
sN Parameter: 0.98
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2-methyl-but-1-ene
dichloromethaneN  Parameter: 1.00
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

trimethyl(prenyl)silane
dichloromethaneN  Parameter: 0.90
sN Parameter: 1.17
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2-methyl-pent-1-ene
dichloromethaneN  Parameter: 0.84
sN Parameter: 1.06
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

2,4,4-trimethyl-pent-1-ene
dichloromethaneN  Parameter: 0.79
sN Parameter: 1.07
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

styrene
dichloromethaneN  Parameter: 0.78
sN Parameter: 0.95
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

(1S)-(-)-alpha-pinene
dichloromethaneN  Parameter: 0.68
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2,4,6-trimethylstyrene
dichloromethaneN  Parameter: 0.68
sN Parameter: 1.09
***Macromolecules 2005, 38, 33-40
DOI: 10.1021/ma048389o
image of molecule

cyclohexa-1,3-diene
dichloromethaneN  Parameter: 0.67
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(Z)-penta-1,3-diene
dichloromethaneN  Parameter: 0.66
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-methyl-but-2-ene
dichloromethaneN  Parameter: 0.65
sN Parameter: 1.17
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2,3-dimethyl-but-1-ene
dichloromethaneN  Parameter: 0.65
sN Parameter: 1.00
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

alpha-(pentamethyldisilyl)styrene
dichloromethaneN  Parameter: 0.61
sN Parameter: 1.01
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

2-(tris(pentafluorophenyl)siloxy)-propene
dichloromethaneN  Parameter: 0.58
sN Parameter: 0.91
*Eur. J. Org. Chem. 2005, , 1760-1764
DOI: 10.1002/ejoc.200400706
image of molecule

2,4-dimethyl-penta-1,4-diene
dichloromethaneN  Parameter: 0.54
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-diazobenzothiophen-3(2H)-one
dichloromethaneN  Parameter: 0.40
sN Parameter: 0.93
***Eur. J. Org. Chem. 2023, 26, e202300005
DOI: 10.1002/ejoc.202300005
image of molecule

(2-methylallyl)benzene
dichloromethaneN  Parameter: 0.25
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-diazoindandione
dichloromethaneN  Parameter: 0.16
sN Parameter: 0.86
***Eur. J. Org. Chem. 2023, 26, e202300005
DOI: 10.1002/ejoc.202300005
image of molecule

3-methylanisole
dichloromethaneN  Parameter: 0.13
sN Parameter: 1.27
***J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

1-methylcyclohexene
dichloromethaneN  Parameter: 0.08
sN Parameter: 1.15
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2,3,3-trimethyl-but-1-ene
dichloromethaneN  Parameter: 0.06
sN Parameter: 1.07
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

cyclohepta-1,3-diene
dichloromethaneN  Parameter: 0.06
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

phenylacetylene
dichloromethaneN  Parameter: -0.04
sN Parameter: 0.77
***Angew. Chem. Int. Ed. 2014, 53, 4968-4971
DOI: 10.1002/anie.201402055
image of molecule

(1H-inden-1-yl)trimethylsilane (in CH2Cl2)
dichloromethaneN  Parameter: -0.10
sN Parameter: 1.05
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
DOI: 10.1002/anie.201501385
image of molecule

allyltriphenylsilane
dichloromethaneN  Parameter: -0.13
sN Parameter: 1.21
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

norbornene
dichloromethaneN  Parameter: -0.25
sN Parameter: 1.09
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

2-(pentamethyldisilyl)propene
dichloromethaneN  Parameter: -0.26
sN Parameter: 0.95
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

2-(tris(trimethylsilyl)silyl)propene
dichloromethaneN  Parameter: -0.31
sN Parameter: 0.99
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

diethyl diazomalonate
dichloromethaneN  Parameter: -0.35
sN Parameter: 0.93
**Chem. Eur. J. 2003, 9, 4068-4076
DOI: 10.1002/chem.200304913
image of molecule

beta-(trimethylsilyl)styrene
dichloromethaneN  Parameter: -0.43
sN Parameter: 1.06
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

1-ethinylcyclohexenyl-Co2(CO)6
dichloromethaneN  Parameter: -0.44
sN Parameter: 1.06
***J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

methylenecyclopropane
dichloromethaneN  Parameter: -0.47
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(E)-propenylbenzene
dichloromethaneN  Parameter: -0.49
sN Parameter: 1.18
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

cycloocta-1,3-diene
dichloromethaneN  Parameter: -0.50
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

allylchlorodimethylsilane
dichloromethaneN  Parameter: -0.57
sN Parameter: 1.06
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

(2-methylallyl)trichlorosilane
dichloromethaneN  Parameter: -0.57
sN Parameter: 0.95
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)
dichloromethaneN  Parameter: -0.64
sN Parameter: 1.10
***J. Am. Chem. Soc. 2017, 139, 15324-15327
DOI: 10.1021/jacs.7b10240
image of molecule

1-(p-tolyl)-1-(trimethylsilyl)ethene
dichloromethaneN  Parameter: -0.65
sN Parameter: 1.59
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)
dichloromethaneN  Parameter: -0.76
sN Parameter: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

2-(trimethylsilyl)thiophene
dichloromethaneN  Parameter: -0.80
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

buta-1,3-diene
dichloromethaneN  Parameter: -0.87
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

tetramethylethylene
dichloromethaneN  Parameter: -1.00
sN Parameter: 1.40
***Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

thiophene
dichloromethaneN  Parameter: -1.01
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(Z)-phenylpropene
dichloromethaneN  Parameter: -1.07
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6
dichloromethaneN  Parameter: -1.11
sN Parameter: 0.92
***J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

alpha-(trimethylsilyl)styrene
dichloromethaneN  Parameter: -1.13
sN Parameter: 1.46
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

anisole
dichloromethaneN  Parameter: -1.18
sN Parameter: 1.20
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

dimethyl diazomalonate
dichloromethaneN  Parameter: -1.24
sN Parameter: 0.81
***Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957
DOI: 10.1002/anie.199409381
image of molecule

2-(trimethylsilyl)propene
dichloromethaneN  Parameter: -1.46
sN Parameter: 1.05
***Chem. Eur. J. 2014, 20, 1103-1110
DOI: 10.1002/chem.201303215
image of molecule

cyclopentene
dichloromethaneN  Parameter: -1.55
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

propene
dichloromethaneN  Parameter: -2.41
sN Parameter: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

(Z)-but-2-ene
dichloromethaneN  Parameter: -2.44
sN Parameter: 1.09
**J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

(E)-but-2-ene
dichloromethaneN  Parameter: -2.45
sN Parameter: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
DOI: 10.1021/ar020094c
image of molecule

1-hexene
dichloromethaneN  Parameter: -2.77
sN Parameter: 1.41
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

3,3,3-trifluoro-2-(trimethylsiloxy)propene
dichloromethaneN  Parameter: -2.94
sN Parameter: 1.11
***Org. Lett. 2012, 14, 3990-3993
DOI: 10.1021/ol301766w
image of molecule

(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene
dichloromethaneN  Parameter: -3.52
sN Parameter: 1.17
***Org. Lett. 2012, 14, 3990-3993
DOI: 10.1021/ol301766w
image of molecule

m-xylene
dichloromethaneN  Parameter: -3.57
sN Parameter: 2.08
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
DOI: 10.1021/ja010890y
image of molecule

2-chloropropene
dichloromethaneN  Parameter: -3.65
sN Parameter: 1.97
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
image of molecule

toluene
dichloromethaneN  Parameter: -4.36
sN Parameter: 1.77
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b