Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
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
2,2,2-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
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
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
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
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
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
formohydrazide (in MeCN)	MeCN	N Param.: 10.35 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
tributyl phosphite	dichloromethane	N Param.: 10.36 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
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
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
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
imidazole (in 91M9AN)	MeOH-MeCN mix	N Param.: 10.41 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 10.42 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
MeO-Breslow 1b	THF	N Param.: 10.45 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
quinine	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
borane-4-tBu-pyridine-complex	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
OH- (in water)	water	N Param.: 10.47 s_N Param.: 0.61	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
diazomethane	dichloromethane	N Param.: 10.48 s_N Param.: 0.78	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
tert-butylamine (in water)	water	N Param.: 10.48 s_N Param.: 0.65	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
4-chloropyridine (in H2O)	water	N Param.: 10.50 s_N Param.: 0.73	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
benzimidazole (in DMSO)	DMSO	N Param.: 10.50 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
2-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 10.52 s_N Param.: 0.78	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
quinidine	dichloromethane	N Param.: 10.54 s_N Param.: 0.74	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine	MeCN	N Param.: 10.56 s_N Param.: 1.01	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran	dichloromethane	N Param.: 10.61 s_N Param.: 0.86	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN)	MeCN	N Param.: 10.63 s_N Param.: 0.84	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
2,4-dimethylpyrrole	MeCN	N Param.: 10.67 s_N Param.: 0.91	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
N-benzyl-1,4-dihydronicotineamide (in 80W20AN)	water-MeCN mix	N Param.: 10.67 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
NADPH (in water)	water	N Param.: 10.68 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
anion of 2-nitropropane (in water)	water	N Param.: 10.69 s_N Param.: 0.56	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
5-methyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.69 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-(phenylmethylamino)cyclohexene	dichloromethane	N Param.: 10.73 s_N Param.: 0.81	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
uracil anion (in water)	water	N Param.: 10.75 s_N Param.: 0.53	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
(E)-beta-(N-morpholino)styrene	dichloromethane	N Param.: 10.76 s_N Param.: 0.87	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
9-methyl guanine anion (in water)	water	N Param.: 10.77 s_N Param.: 0.65	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411