N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
imidazole (in MeCN)	MeCN	N Param.: 11.47 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
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
hydroxylamine (in water)	water	N Param.: 11.41 s_N Param.: 0.55	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
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
ammonia (in MeCN)	MeCN	N Param.: 11.39 s_N Param.: 0.69	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
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
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
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
thymine anion (in water)	water	N Param.: 11.17 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
N-(phenylmethyl)propan-2-imine (in CH2Cl2)	dichloromethane	N Param.: 11.13 s_N Param.: 0.73	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
4-amino-3,5-dibromo-pyridine (in MeCN)	MeCN	N Param.: 11.11 s_N Param.: 0.75	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-methylpyridine (in H2O)	water	N Param.: 11.10 s_N Param.: 0.75	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
5,6-dimethyl-benzimidazole (in DMSO)	DMSO	N Param.: 11.08 s_N Param.: 0.71	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-formyl-imidazole anion (in water)	water	N Param.: 11.07 s_N Param.: 0.50	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
semicarbazide (in water)	water	N Param.: 11.05 s_N Param.: 0.52	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
pyridine (in H2O)	water	N Param.: 11.05 s_N Param.: 0.73	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
5-methoxy-benzimidazole (in DMSO)	DMSO	N Param.: 11.00 s_N Param.: 0.71	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
purine anion (in water)	water	N Param.: 11.00 s_N Param.: 0.54	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2-methylpyridine (in MeCN)	MeCN	N Param.: 10.98 s_N Param.: 0.66	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
adenine anion (in water)	water	N Param.: 10.93 s_N Param.: 0.62	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
3-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 10.90 s_N Param.: 0.93	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
6-methoxy-quinoline (in MeCN)	MeCN	N Param.: 10.86 s_N Param.: 0.66	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
(S)-3,3-difluoro-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine (in CH2Cl2)	dichloromethane	N Param.: 10.83 s_N Param.: 0.80	ARKIVOC 2024, (4), 202312093 10.24820/ark.5550190[...]
glycinenitrile (in water)	water	N Param.: 10.80 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
saccharin anion (in MeCN)	MeCN	N Param.: 10.78 s_N Param.: 0.89	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
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
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
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
quinidine	dichloromethane	N Param.: 10.54 s_N Param.: 0.74	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
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
tert-butylamine (in water)	water	N Param.: 10.48 s_N Param.: 0.65	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
quinine	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
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-methyl-benzimidazole (in MeCN)	MeCN	N Param.: 10.37 s_N Param.: 0.82	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
formohydrazide (in MeCN)	MeCN	N Param.: 10.35 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
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
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
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
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
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-methyl-imidazole (in water)	water	N Param.: 9.91 s_N Param.: 0.55	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
(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
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
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