Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2)	dichloromethane	N Param.: 9.81 s_N Param.: 0.77	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2,6-dimethylpyridine (in CH2Cl2)	dichloromethane	N Param.: 9.87 s_N Param.: 0.68	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
(S)-2-(azidodiphenylmethyl)pyrrolidine	MeCN	N Param.: 9.90 s_N Param.: 1.22	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
1-methyl-imidazole (in water)	water	N Param.: 9.91 s_N Param.: 0.55	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN)	MeCN	N Param.: 9.94 s_N Param.: 0.86	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
tributylstannane	dichloromethane	N Param.: 9.96 s_N Param.: 0.55	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
alpha-(N-morpholino)styrene	dichloromethane	N Param.: 9.96 s_N Param.: 0.79	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
cyanoborate ion (in water)	water	N Param.: 9.99 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
2-(p-anisyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.01 s_N Param.: 0.72	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
borane-pyridine-complex	dichloromethane	N Param.: 10.01 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-methyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.02 s_N Param.: 0.85	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)	dichloromethane	N Param.: 10.03 s_N Param.: 0.75	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
morpholinoisobutylene	dichloromethane	N Param.: 10.04 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
[H-B(C6F5)3]- [NEt4]+	MeCN	N Param.: 10.04 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298
theophylline anion (in water)	water	N Param.: 10.06 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
chloride (in H2O)	water	N Param.: 10.10 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
2,2,2-trifluoroethylamine (in MeCN)	MeCN	N Param.: 10.13 s_N Param.: 0.75	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate	MeCN	N Param.: 10.13 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
2-(p-tolyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.14 s_N Param.: 0.70	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
OH- (in 50/50 water/MeCN)	water-MeCN mix	N Param.: 10.19 s_N Param.: 0.62	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y