Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
chloride (in 20% aq MeCN)	water-MeCN mix	N Param.: 11.31 s_N Param.: 0.58	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
1-phenyl-imidazole (in MeCN)	MeCN	N Param.: 11.31 s_N Param.: 0.67	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
fluoride (in MeOH)	MeOH	N Param.: 11.31 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
2-(trifluoromethyl)pyrrolidine	MeCN	N Param.: 11.34 s_N Param.: 0.73	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
N-benzyl-1,4-dihydronicotineamide (in 90W10AN)	water-MeCN mix	N Param.: 11.35 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
4-nitro-imidazole anion (in water)	water	N Param.: 11.37 s_N Param.: 0.53	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
ammonia (in MeCN)	MeCN	N Param.: 11.39 s_N Param.: 0.69	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
1-(N-morpholino)cyclohexene	dichloromethane	N Param.: 11.40 s_N Param.: 0.83	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
fluoride (in 80% aq MeCN)	water-MeCN mix	N Param.: 11.40 s_N Param.: 0.59	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
tert-butyl hydrazinecarboxylate (in MeCN)	MeCN	N Param.: 11.40 s_N Param.: 0.70	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
hydroxylamine (in water)	water	N Param.: 11.41 s_N Param.: 0.55	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
Desoxy Breslow intermediate 2b'	THF	N Param.: 11.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
1-(trimethylsilyl)-imidazole (in MeCN)	MeCN	N Param.: 11.43 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
4-methoxypyridine (in H2O)	water	N Param.: 11.44 s_N Param.: 0.68	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
imidazole (in MeCN)	MeCN	N Param.: 11.47 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 11.50 s_N Param.: 0.91	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
3-methylpyridine (in MeCN)	MeCN	N Param.: 11.50 s_N Param.: 0.80	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
2,4-dimethyl-imidazole (in MeCN)	MeCN	N Param.: 11.51 s_N Param.: 0.84	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
NaBH3(CN) (in DMSO)	DMSO	N Param.: 11.52 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
benzotriazole anion (in water)	water	N Param.: 11.52 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411