Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
nicotine (in CH2Cl2)	dichloromethane	N Param.: 10.40 s_N Param.: 1.04	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
1,1-bis(trimethylsiloxy)propene	dichloromethane	N Param.: 10.38 s_N Param.: 0.87	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
1-methyl-benzimidazole (in MeCN)	MeCN	N Param.: 10.37 s_N Param.: 0.82	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
NADH (in water)	water	N Param.: 10.37 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
tributyl phosphite	dichloromethane	N Param.: 10.36 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
formohydrazide (in MeCN)	MeCN	N Param.: 10.35 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
borane-2,6-lutidine-complex	dichloromethane	N Param.: 10.33 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene	dichloromethane	N Param.: 10.32 s_N Param.: 0.79	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
chloride (in CF3CH2OH)	TFE	N Param.: 10.30 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
alpha-(N-morpholino)styrene (in MeCN)	MeCN	N Param.: 10.30 s_N Param.: 0.80	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
Ph3P=CH-C(O)Me (in MeCN)	MeCN	N Param.: 10.27 s_N Param.: 0.83	J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264
1-butoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 10.21 s_N Param.: 0.82	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
2,5-dimethyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.21 s_N Param.: 0.85	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2,2,2-trifluoroethylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 10.20 s_N Param.: 0.92	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
2-methyl-4,5-dihydrothiazole (in CH2Cl2)	dichloromethane	N Param.: 10.20 s_N Param.: 0.71	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
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
N-benzyl-1,4-dihydronicotineamide (in 67W33AN)	water-MeCN mix	N Param.: 10.19 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 10.19 s_N Param.: 1.06	J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e
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
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