N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
4-formyl-imidazole anion (in DMSO)  |
DMSO | N Param.: 16.40 sN Param.: 0.67 |  | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzimidazole anion (in DMSO) |
DMSO | N Param.: 19.13 sN Param.: 0.55 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzotriazole anion (in DMSO) |
DMSO | N Param.: 16.29 sN Param.: 0.65 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
purine anion (in DMSO) |
DMSO | N Param.: 15.03 sN Param.: 0.77 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
theophylline anion (in DMSO) |
DMSO | N Param.: 14.78 sN Param.: 0.71 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
adenine anion (in DMSO) |
DMSO | N Param.: 18.00 sN Param.: 0.55 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
uracil anion (in DMSO) |
DMSO | N Param.: 17.04 sN Param.: 0.63 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
thymine anion (in DMSO) |
DMSO | N Param.: 17.63 sN Param.: 0.62 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
1-methyl uracil anion (in DMSO) |
DMSO | N Param.: 16.36 sN Param.: 0.69 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO) |
DMSO | N Param.: 14.58 sN Param.: 0.79 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
azide ion (in 91E9AN) |
EtOH-MeCN mix | N Param.: 16.30 sN Param.: 0.73 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91iPr9AN) |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
thiocyanate (in MeCN) |
MeCN | N Param.: 12.13 sN Param.: 0.60 | | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
nitrite ion (in MeCN) |
MeCN | N Param.: 17.20 sN Param.: 0.72 | | Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274 |
4-(dimethylamino)pyridine (in MeCN) |
MeCN | N Param.: 15.51 sN Param.: 0.62 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
4-chloroaniline (in MeCN) |
MeCN | N Param.: 12.92 sN Param.: 0.60 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in MeCN) |
MeCN | N Param.: 12.64 sN Param.: 0.68 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
p-toluidine (in MeCN) |
MeCN | N Param.: 13.19 sN Param.: 0.69 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
4-methoxyaniline (in MeCN) |
MeCN | N Param.: 13.42 sN Param.: 0.73 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
DABCO (in MeCN) |
MeCN | N Param.: 18.80 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
quinuclidine (in MeCN) |
MeCN | N Param.: 20.54 sN Param.: 0.60 | | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
DBU (in MeCN) |
MeCN | N Param.: 15.29 sN Param.: 0.70 | | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
DBN (in MeCN) |
MeCN | N Param.: 16.28 sN Param.: 0.67 | | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
cyanate (in MeCN) |
MeCN | N Param.: 13.60 sN Param.: 0.84 | | Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 |
6-methoxy-quinoline (in MeCN) |
MeCN | N Param.: 10.86 sN Param.: 0.66 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
4-methyl-quinoline alias lepidine (in MeCN) |
MeCN | N Param.: 11.60 sN Param.: 0.62 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
2-(naphthylmethyl)quinuclidine (in MeCN) |
MeCN | N Param.: 15.66 sN Param.: 0.62 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
2,2,2-trifluoroethylamine (in MeCN) |
MeCN | N Param.: 10.13 sN Param.: 0.75 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
tert-butylamine (in MeCN) |
MeCN | N Param.: 12.35 sN Param.: 0.72 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
isopropylamine (in MeCN) |
MeCN | N Param.: 13.77 sN Param.: 0.70 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
ethanolamine (in MeCN) |
MeCN | N Param.: 14.11 sN Param.: 0.71 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
benzylamine (in MeCN) |
MeCN | N Param.: 14.29 sN Param.: 0.67 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
allylamine (in MeCN) |
MeCN | N Param.: 14.37 sN Param.: 0.66 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
n-propylamine (in MeCN) |
MeCN | N Param.: 15.11 sN Param.: 0.63 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
n-butylamine (in MeCN) |
MeCN | N Param.: 15.27 sN Param.: 0.63 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
dipropylamine (in MeCN) |
MeCN | N Param.: 14.51 sN Param.: 0.80 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
diethylamine (in MeCN) |
MeCN | N Param.: 15.10 sN Param.: 0.73 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
morpholine (in MeCN) |
MeCN | N Param.: 15.65 sN Param.: 0.74 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
piperidine (in MeCN) |
MeCN | N Param.: 17.35 sN Param.: 0.68 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
di(methoxyethyl)amine (in MeCN) |
MeCN | N Param.: 13.24 sN Param.: 0.93 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
imidazole (in MeCN) |
MeCN | N Param.: 11.47 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.90 sN Param.: 0.73 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-phenyl-imidazole (in MeCN) |
MeCN | N Param.: 11.31 sN Param.: 0.67 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.74 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
4-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.79 sN Param.: 0.77 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2,4-dimethyl-imidazole (in MeCN) |
MeCN | N Param.: 11.51 sN Param.: 0.84 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-(trimethylsilyl)-imidazole (in MeCN) |
MeCN | N Param.: 11.43 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-benzimidazole (in MeCN) |
MeCN | N Param.: 10.37 sN Param.: 0.82 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
benzotriazole (in MeCN) |
MeCN | N Param.: 7.69 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-benzotriazole (in MeCN) |
MeCN | N Param.: 7.77 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
triethylamine (in MeCN) |
MeCN | N Param.: 17.10 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-pyrrolidine (in MeCN) |
MeCN | N Param.: 20.59 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-piperidine (in MeCN) |
MeCN | N Param.: 18.72 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-morpholine (in MeCN) |
MeCN | N Param.: 16.80 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
2-pyridone anion (in MeCN) |
MeCN | N Param.: 20.11 sN Param.: 0.57 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in MeCN) |
MeCN | N Param.: 20.22 sN Param.: 0.49 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
saccharin anion (in MeCN) |
MeCN | N Param.: 10.78 sN Param.: 0.89 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
2-Me super-dmap (in MeCN) |
MeCN | N Param.: 16.65 sN Param.: 0.58 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Et super-dmap (in MeCN) |
MeCN | N Param.: 16.81 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bn super-dmap (in MeCN) |
MeCN | N Param.: 17.69 sN Param.: 0.57 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Ac super-dmap (in MeCN) |
MeCN | N Param.: 15.39 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bz super-dmap (in MeCN) |
MeCN | N Param.: 14.19 sN Param.: 0.67 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
hydrazine (in MeCN) |
MeCN | N Param.: 16.45 sN Param.: 0.56 | | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
1,1-dimethylhydrazine (in MeCN) |
MeCN | N Param.: 11.72 sN Param.: 0.73 | | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
trimethylhydrazine (in MeCN) |
MeCN | N Param.: 12.43 sN Param.: 0.75 | | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
1,1-dimethylhydrazine (in MeCN) |
MeCN | N Param.: 22.41 sN Param.: 0.45 | | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
trimethylhydrazine (in MeCN) |
MeCN | N Param.: 17.75 sN Param.: 0.53 | | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
acetonitrile (in MeCN) |
MeCN | N Param.: 2.23 sN Param.: 0.84 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
4-(morpholino)pyridine (in MeCN) |
MeCN | N Param.: 14.80 sN Param.: 0.63 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
3-bromo-4-(dimethylamino)pyridine (in MeCN) |
MeCN | N Param.: 12.96 sN Param.: 0.67 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
4-amino-3,5-dibromo-pyridine (in MeCN) |
MeCN | N Param.: 11.11 sN Param.: 0.75 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
4-acetamido-pyridine (in MeCN) |
MeCN | N Param.: 13.24 sN Param.: 0.67 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
methylhydrazine (in MeCN) |
MeCN | N Param.: 17.73 sN Param.: 0.58 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
1,2-dimethylhydrazine (in MeCN) |
MeCN | N Param.: 16.15 sN Param.: 0.68 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
formohydrazide (in MeCN) |
MeCN | N Param.: 10.35 sN Param.: 0.76 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
N',N'-dimethylformohydrazide (in MeCN) |
MeCN | N Param.: 15.69 sN Param.: 0.51 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
tert-butyl hydrazinecarboxylate (in MeCN) |
MeCN | N Param.: 11.40 sN Param.: 0.70 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
benzohydrazide (in MeCN) |
MeCN | N Param.: 12.49 sN Param.: 0.66 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
hydroxylamine (in MeCN) |
MeCN | N Param.: 12.80 sN Param.: 0.63 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
N-methylhydroxylamine (in MeCN) |
MeCN | N Param.: 14.10 sN Param.: 0.76 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
ammonia (in MeCN) |
MeCN | N Param.: 11.39 sN Param.: 0.69 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
methylamine (in MeCN) |
MeCN | N Param.: 15.19 sN Param.: 0.68 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
dimethylamine (in MeCN) |
MeCN | N Param.: 17.96 sN Param.: 0.63 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
trimethylamine (in MeCN) |
MeCN | N Param.: 23.05 sN Param.: 0.45 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN) |
MeCN | N Param.: 14.43 sN Param.: 0.79 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
nicotine (in MeCN) |
MeCN | N Param.: 11.60 sN Param.: 0.81 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
3-methylpyridine (in MeCN) |
MeCN | N Param.: 11.50 sN Param.: 0.80 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
1-methyl-2-phenylpyrrolidine (in MeCN) |
MeCN | N Param.: 15.70 sN Param.: 0.54 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
prolinate (in MeCN) |
MeCN | N Param.: 19.95 sN Param.: 0.68 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-methylpyrrolidine (in MeCN) |
MeCN | N Param.: 16.78 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
pyrrolidine (inMeCN) |
MeCN | N Param.: 18.58 sN Param.: 0.61 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(R)-2-isopropylpyrrolidine |
MeCN | N Param.: 16.44 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,2-dimethylpyrrolidine |
MeCN | N Param.: 13.96 sN Param.: 0.76 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-benzylpyrrolidine |
MeCN | N Param.: 17.43 sN Param.: 0.66 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-benzhydrylpyrrolidine |
MeCN | N Param.: 16.61 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanamine |
MeCN | N Param.: 17.24 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine |
MeCN | N Param.: 17.41 sN Param.: 0.68 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine |
MeCN | N Param.: 18.33 sN Param.: 0.64 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(azidomethyl)pyrrolidine |
MeCN | N Param.: 15.43 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanol |
MeCN | N Param.: 16.74 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |