Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
methyl carbonate (in MeCN)	MeCN	N Param.: 16.03 s_N Param.: 0.64	Eur. J. Org. Chem. 2010, , 4205-4210 10.1002/ejoc.201000414
anion of 1-phenylbutane-1,3-dione (in DMSO)	DMSO	N Param.: 16.03 s_N Param.: 0.86	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
diacetamide anion (in DMSO)	DMSO	N Param.: 16.05 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
2-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.06 s_N Param.: 0.68	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)	DMSO	N Param.: 16.06 s_N Param.: 0.69	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
ethanolamine (in DMSO)	DMSO	N Param.: 16.07 s_N Param.: 0.61	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
ethanolate (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.08 s_N Param.: 0.62	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
Se-HyperBTM (in DCM)	dichloromethane	N Param.: 16.11 s_N Param.: 0.58	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
DBU (in THF)	THF	N Param.: 16.12 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
anion of diethyl malonate (in water)	water	N Param.: 16.15 s_N Param.: 0.66	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)	dichloromethane	N Param.: 16.15 s_N Param.: 0.73	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1,2-dimethylhydrazine (in MeCN)	MeCN	N Param.: 16.15 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)	MeCN	N Param.: 16.15 s_N Param.: 0.99	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine	dichloromethane	N Param.: 16.16 s_N Param.: 0.75	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
tris(4-methoxyphenyl)phosphane	dichloromethane	N Param.: 16.17 s_N Param.: 0.62	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
(S)-diphenyl(pyrrolidin-2-yl)methanol	MeCN	N Param.: 16.18 s_N Param.: 0.56	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
Me2S=CH-CN (in DMSO)	DMSO	N Param.: 16.23 s_N Param.: 0.60	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)	DMSO	N Param.: 16.26 s_N Param.: 0.83	J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147
anion of dimedone (in DMSO)	DMSO	N Param.: 16.27 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
cyanide (in MeCN)	MeCN	N Param.: 16.27 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640