Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
diethylamine (in water)	water	N Param.: 14.68 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
chloride (in EtOH)	EtOH	N Param.: 14.70 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
NaBH4 (in DMSO)	DMSO	N Param.: 14.74 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
anion of (3-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.75 s_N Param.: 0.71	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
methyl L-prolinate	MeCN	N Param.: 14.75 s_N Param.: 0.82	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
4-pyridone anion (in water)	water	N Param.: 14.76 s_N Param.: 0.48	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
MeO-Breslow 1a	THF	N Param.: 14.77 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
theophylline anion (in DMSO)	DMSO	N Param.: 14.78 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-(dimethylamino)pyridine (in DMSO)	DMSO	N Param.: 14.80 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(morpholino)pyridine (in MeCN)	MeCN	N Param.: 14.80 s_N Param.: 0.63	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-nitro-imidazole anion (in DMSO)	DMSO	N Param.: 14.81 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
maleimide anion (in DMSO)	DMSO	N Param.: 14.87 s_N Param.: 0.76	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
tris(2,4-dimethylphenyl)phosphane	dichloromethane	N Param.: 14.88 s_N Param.: 0.41	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
4-(dimethylamino)pyridine (in DMF)	DMF	N Param.: 14.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
3,5-dinitrobenzoate (in MeCN)	MeCN	N Param.: 14.90 s_N Param.: 0.71	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
1,3-diethyl-thiobarbiturate anion (in DMSO)	DMSO	N Param.: 14.90 s_N Param.: 0.80	J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223
1-(N-pyrrolidino)cyclohexene	dichloromethane	N Param.: 14.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
Bu4NBH4 (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.96	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
methyl (cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 14.96 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344