Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
methanolate (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.51 s_N Param.: 0.68	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
azide ion (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.54 s_N Param.: 0.82	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine	dichloromethane	N Param.: 14.57 s_N Param.: 0.75	Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)	DMSO	N Param.: 14.58 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
4-(morpholino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 14.59 s_N Param.: 0.69	Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.72	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
ITeU2	dichloromethane	N Param.: 14.62 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, , in print 10.1002/anie.202514865
tricyclohexylphosphane	dichloromethane	N Param.: 14.64 s_N Param.: 0.68	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
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