Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
quinidine	dichloromethane	N Param.: 10.54 s_N Param.: 0.74	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
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
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
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
OH- (in water)	water	N Param.: 10.47 s_N Param.: 0.61	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
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
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
(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
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
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