Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
chloride (in MeOH)	MeOH	N Param.: 12.90 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
pyridine (in CH2Cl2)	dichloromethane	N Param.: 12.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
ethylamine (in water)	water	N Param.: 12.87 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
bromide (in 40% aq MeCN)	water-MeCN mix	N Param.: 12.80 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
hydroxylamine (in MeCN)	MeCN	N Param.: 12.80 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
Ph3P=CH-CO2Et	dichloromethane	N Param.: 12.79 s_N Param.: 0.77	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
Desoxy Breslow intermediate 2c'	THF	N Param.: 12.75 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
bromite (in water)	water	N Param.: 12.75 s_N Param.: 0.59	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
acetate (in 90A10W)	aq acetone	N Param.: 12.71 s_N Param.: 0.68	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
dimethylsulfide (in MeCN)	MeCN	N Param.: 12.70 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
threonine (anionic, in water)	water	N Param.: 12.69 s_N Param.: 0.60	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
2,2,2-trifluoroethanolate (in water)	water	N Param.: 12.66 s_N Param.: 0.59	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
aniline (in MeCN)	MeCN	N Param.: 12.64 s_N Param.: 0.68	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethanolamine (in water)	water	N Param.: 12.61 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
dimethylselenide (in CH2Cl2)	dichloromethane	N Param.: 12.60 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
tris(4-chlorophenyl)phosphane	dichloromethane	N Param.: 12.58 s_N Param.: 0.65	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
5-(trimethylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 12.56 s_N Param.: 0.70	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(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
7-Ms-HyperBTM	dichloromethane	N Param.: 12.52 s_N Param.: 0.75	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
1-(1-cyclohexenyl)-4-methylpiperazine	dichloromethane	N Param.: 12.51 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666