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Name	Solvent	Reactivity Parameters	Reference (title or year)
o-nitrophenolate (in DMF)	DMF	N Param.: 16.65 s_N Param.: 0.70	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-nitrophenolate (in DMSO)	DMSO	N Param.: 15.48 s_N Param.: 0.71	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrophenolate (in DMF)	DMF	N Param.: 15.05 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrophenolate (in MeCN)	MeCN	N Param.: 15.14 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-nitrophenolate (in MeCN)	MeCN	N Param.: 15.83 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
cysteine (dianionic, in water)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)	MeCN	E Param.: -3.66	J. Am. Chem. Soc. 2013, 135, 12377-12387 10.1021/ja405890d
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 6.24 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
potassium trifluoro(furan-2-yl)borate	MeCN	N Param.: 5.99 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
((2-(2-iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane		E Param.: -14.52	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane		E Param.: -13.77	Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in CH2Cl2)	dichloromethane	N Param.: 19.63 s_N Param.: 0.65	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 17.28 s_N Param.: 0.65	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
((dimethylsilyl)methyl)trimethylsilane	dichloromethane	N Param.: 4.86 s_N Param.: 0.64	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
((methylsilanediyl)bis(methylene))bis(trimethylsilane)	dichloromethane	N Param.: 4.91 s_N Param.: 0.64	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(1H-inden-1-yl)trimethylsilane (in CH2Cl2)	dichloromethane	N Param.: -0.10 s_N Param.: 1.05	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)trimethylstannane (in CH2Cl2)	dichloromethane	N Param.: 6.68 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO)	DMSO	N Param.: 15.60 s_N Param.: 0.51	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO)	DMSO	N Param.: 18.10 s_N Param.: 0.46	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
(1S)-(-)-alpha-pinene	dichloromethane	N Param.: 0.68 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2,2-diphenylethyl)diethyl(methyl)silane	dichloromethane	N Param.: -6.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(2,3-dimethylbut-2-enyl)triethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 1.15	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2,4,6-trimethylphenyl)ethylium ion		E Param.: 6.04	Macromolecules 2005, 38, 33-40 10.1021/ma048389o
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene	DMSO	E Param.: -13.88	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
(2-([1,1'-biphenyl]-4-yl)ethyl)trimethylstannane	1,2-dichloroethane	N Param.: -0.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(2-methylallyl)benzene	dichloromethane	N Param.: 0.25 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 8.45 s_N Param.: 0.83	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
(2-methylallyl)tributylstannane	dichloromethane	N Param.: 7.48 s_N Param.: 0.89	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)trichlorosilane	dichloromethane	N Param.: -0.57 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)trimethylsilane	dichloromethane	N Param.: 4.41 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)triphenylgermane	dichloromethane	N Param.: 4.67 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)triphenylsilane	dichloromethane	N Param.: 4.17 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)triphenylstannane	dichloromethane	N Param.: 5.13 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-methylallyl)tris(trimethylsilyl)silane	dichloromethane	N Param.: 4.63 s_N Param.: 0.87	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(2-phenylethene-1,1-diyldisulfonyl)dibenzene	DMSO	E Param.: -12.93	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one	MeCN	N Param.: 7.39 s_N Param.: 1.00	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one	MeCN	N Param.: 5.80 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one	MeCN	N Param.: 5.44 s_N Param.: 1.12	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one	MeCN	N Param.: 8.76 s_N Param.: 0.89	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(2S,5S)-5-benzyl-3-methyl-4-oxo-1-(3-phenylallylidene)-2-((E)-styryl)imidazolidin-1-ium	dichloromethane	E Param.: -5.90	Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene	dichloromethane	N Param.: -3.52 s_N Param.: 1.17	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
(3-CF3)-tritylium ion		E Param.: 1.18	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(3-chlorobenzyl)dimethylsilane	dichloromethane	N Param.: 1.30 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(3-Cl)-tritylium ion		E Param.: 1.06	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(3-Cl)3-tritylium ion		E Param.: 1.99	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(3-F)-tritylium ion		E Param.: 1.01	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(3-F)2-tritylium ion		E Param.: 1.54	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(3-F)3-tritylium ion		E Param.: 2.07	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(3-F)4-tritylium ion		E Param.: 2.54	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(4,4-dimethylpentyl)trimethylstannane	dichloromethane/MeCN mix	N Param.: -3.90 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-(tert-butyl)phenethyl)trimethylstannane	1,2-dichloroethane	N Param.: -0.30 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-Br-C6H4)-(CO)-CH=SMe2	dichloromethane	N Param.: 11.95 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.78 s_N Param.: 0.72	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-CF3)-tritylium ion		E Param.: 1.33	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-CF3)2-tritylium ion		E Param.: 2.28	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-chlorophenethyl)trimethylstannane	1,2-dichloroethane	N Param.: -1.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-chlorophenyl)dimethylsilane	dichloromethane	N Param.: 3.05 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-F)-tritylium ion		E Param.: 0.35	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(4-F)2-tritylium ion		E Param.: 0.17	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(4-F)3-tritylium ion		E Param.: 0.05	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(4-Me)-tritylium ion		E Param.: -0.13	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-Me)2-tritylium ion		E Param.: -0.70	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-Me)3-tritylium ion		E Param.: -1.21	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 15.68 s_N Param.: 0.65	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-MeO)-tritylium ion		E Param.: -1.59	Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910
(4-MeO)2-tritylium ion		E Param.: -3.04	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-MeO)3-tritylium ion		E Param.: -4.35	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-MeO,3-OMe)-tritylium ion		E Param.: -1.62	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-MeO,4-Me)-tritylium ion		E Param.: -2.13	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 14.48 s_N Param.: 0.71	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-methoxyphenethyl)trimethylstannane	1,2-dichloroethane	N Param.: 0.20 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-methoxyphenyl)dimethylsilane	dichloromethane	N Param.: 4.23 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-NMe2)-tritylium ion		E Param.: -7.93	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-NMe2)2-tritylium ion (= Malachite green)		E Param.: -10.29	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-NMe2)3-tritylium ion (= Crystal violet)		E Param.: -11.26	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(4-OMe,3-Me)-tritylium ion		E Param.: -1.84	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
(5-methyl-furan-2-yl) MDA boronate	MeCN	N Param.: 6.38 s_N Param.: 0.86	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) MIDA boronate	MeCN	N Param.: 1.84 s_N Param.: 1.26	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) pinacol boronate	MeCN	N Param.: 2.90 s_N Param.: 0.98	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) trifluoroborate	MeCN	N Param.: 7.66 s_N Param.: 1.04	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate	MeCN	N Param.: 12.55 s_N Param.: 0.92	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(allyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 6.78 s_N Param.: 0.95	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
(ani)2CH+		E Param.: 0.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(bis(trimethylsiloxy)amino)styrene	dichloromethane	N Param.: 4.80 s_N Param.: 0.86	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
(C6H5)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.95 s_N Param.: 0.69	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(chloromethyl)dimethylsilane	dichloromethane	N Param.: 0.80 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(Cp*)2Zr(Me)2 - Dimethyl-bis(pentamethylcyclopentadienyl)zirconium	dichloromethane	N Param.: 5.49 s_N Param.: 1.06	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
(cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 18.86 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
(dfp)(mfp)CH+		E Param.: 7.52	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
(dfp)2CH+		E Param.: 8.02	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
(dfp)PhCH+		E Param.: 6.74	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
(dma)2CH+		E Param.: -7.02	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(dpa)2CH+		E Param.: -4.72	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(E)-1,2-dimethyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion		E Param.: -5.05	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
(E)-1,3-diphenylprop-2-en-1-one (in DMSO)	DMSO	E Param.: -19.39	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN)	MeCN	N Param.: 9.94 s_N Param.: 0.86	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(1,2-diphenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 11.66 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(2-(4-methoxyphenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 11.99 s_N Param.: 0.84	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 10.42 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(N-morpholino)propene	dichloromethane	N Param.: 12.06 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666

News

11/05/25:
Isochalcogenoureas (O, S, Se & Te derivatives) have been added (Angew. Chem. Int. Ed. 2025, EarlyView, e202514865).
01/30/25:
Sesamol-derived ortho-quinone methides (o-QM) have been added (ChemEurJ 2024, e202403785 & OBC 2025, 23, 827-834)
05/22/24:
Lactone enolates have been added (JOC 2024, 89, 6915-6928).
11/13/24:
2-Methylene-1,2-dihydropyridines (2-pyNHOs) have been added (EurJOC 2024, 27, e202400373).
05/21/24:
Mesoionic pyridinium-derived N-heterocyclic olefins (py-mNHOs) have been added (Angew. Chem. Int. Ed. 2024, 63, e202318283).
10/19/23:
Enamines derived from 4-(alkylthio)-3-imidazolines and aldehydes have been added (ChemEurJ 2023, doi: 10.1002/chem.202302764).
09/28/23:
Mesoionic N-heterocyclic olefins (mNHOs) have been added (Angew. Chem. Int. Ed. 2023, 62, e202309790).
07/05/23:
S-Cyanomethylated imidazolidine-4-thione-derived enamines have been added (ChemComm 2023, 59, 8091).
03/16/23:
Cyclic alpha-diazo carbonyl compounds added (EurJOC 2023, 26, e202300005)
01/30/23:
NADH and NADPH reactivities (in water, pH 7) determined by Mayer and Moran have been added (OBC 2022, 21, 85-88).
09/20/22:
Alkenyl boronate nucleophilicity by Liu, Ready and co-workers has been added (JACS 2022, 144, 16118).
01/30/23:
Electrophilicities of diazo compounds in azo couplings (ChemEurJ 2022, 28, e202201376)
01/30/23:
Diazocyclopentadiene added (Synthesis 2023, 55, 354-358)
01/30/23:
Electrophilic indoles added (ChemCommun 2021, 57, 10071-10074)
04/13/21:
Cyclic Michael acceptors added (Chem. Sci. 2021, 12, 4850-4865)
05/21/21:
Thiophenolates (in DMSO) added (JOC 2021, 86, 5965-5972)
05/06/20:
Heteroallenes added (JACS 2020, 142, 8383-8402).
01/27/20:
Pyrrolidines and Imidazolidinones added (JACS 2020, 142, 1526-1547).
05/06/20:
GSH reactivity added (Angew. Chem. Int. Ed. 2019, 58, 17704-17708)
01/30/23:
Phenolates added (JOC 2019, 84, 8837-8858)
04/24/18:
Ketones added (JACS 2018, 140, 5500).
11/03/17:
Allyl-boron nucleophiles added (JACS 2017, 139, 15324)
04/23/18:
Peroxide anions added (Angew. Chem. Int. Ed. 2017, 56, 13279).
04/23/18:
Michael acceptors added (JACS 2017, 139, 13318).
06/16/17:
Nucleophilicities of VNS reagents (JOC 2017, 82, 1011).