Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
N',N'-dimethylformohydrazide (in MeCN)	MeCN	N Param.: 15.69 s_N Param.: 0.51	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
n-propylamine (in DMSO)	DMSO	N Param.: 15.70 s_N Param.: 0.64	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
N-methyl-trifluoroacetamide anion (in DMSO)	DMSO	N Param.: 15.70 s_N Param.: 0.71	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
1-methyl-2-phenylpyrrolidine (in MeCN)	MeCN	N Param.: 15.70 s_N Param.: 0.54	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
methanolate (in methanol)	MeOH	N Param.: 15.78 s_N Param.: 0.56	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
ethanolate (in ethanol)	EtOH	N Param.: 15.78 s_N Param.: 0.65	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
4-(dimethylamino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 15.80 s_N Param.: 0.66	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
trifluoroacetamide anion (in DMSO)	DMSO	N Param.: 15.81 s_N Param.: 0.64	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
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
Se-HyperBTM (in MeCN)	MeCN	N Param.: 15.84 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Me2S=CH-CO2Et (in DMSO)	DMSO	N Param.: 15.85 s_N Param.: 0.61	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)	DMSO	N Param.: 15.85 s_N Param.: 1.04	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
4-pyrrolidinopyridine (in CH2Cl2)	dichloromethane	N Param.: 15.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in THF)	THF	N Param.: 15.90 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione	MeCN	N Param.: 15.90 s_N Param.: 0.77	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
1-(N-pyrrolidino)cyclopentene	dichloromethane	N Param.: 15.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)	THF	N Param.: 15.92 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
anion of diethyl 2-phenylmalonate (in DMSO)	DMSO	N Param.: 15.93 s_N Param.: 0.99	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
pyrrolidine (in 91M9AN)	MeOH-MeCN mix	N Param.: 15.97 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)	DMSO	N Param.: 15.97 s_N Param.: 0.72	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513