N-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
semicarbazide (in water)![]() ![]() |
water | N Param.: 11.05 sN Param.: 0.52 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
hydroxylamine (in water)![]() ![]() |
water | N Param.: 11.41 sN Param.: 0.55 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
n-propylamine (in water)![]() ![]() |
water | N Param.: 13.33 sN Param.: 0.56 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
4-chloropyridine (in H2O)![]() ![]() |
water | N Param.: 10.50 sN Param.: 0.73 | ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
pyridine (in H2O)![]() ![]() |
water | N Param.: 11.05 sN Param.: 0.73 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-methylpyridine (in H2O)![]() ![]() |
water | N Param.: 11.10 sN Param.: 0.75 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-methoxypyridine (in H2O)![]() ![]() |
water | N Param.: 11.44 sN Param.: 0.68 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-aminopyridine (in H2O)![]() ![]() |
water | N Param.: 12.19 sN Param.: 0.66 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-(dimethylamino)pyridine (in H2O)![]() ![]() |
water | N Param.: 13.19 sN Param.: 0.56 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-pyrrolidinopyridine (in H2O)![]() ![]() |
water | N Param.: 12.39 sN Param.: 0.66 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
ammonia (in water)![]() ![]() |
water | N Param.: 9.48 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
methylamine (in water)![]() ![]() |
water | N Param.: 13.85 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ethylamine (in water)![]() ![]() |
water | N Param.: 12.87 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
isopropylamine (in water)![]() ![]() |
water | N Param.: 12.00 sN Param.: 0.56 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
tert-butylamine (in water)![]() ![]() |
water | N Param.: 10.48 sN Param.: 0.65 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
dimethylamine (in water)![]() ![]() |
water | N Param.: 17.12 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
diethylamine (in water)![]() ![]() |
water | N Param.: 14.68 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
pyrrolidine (in water)![]() ![]() |
water | N Param.: 17.21 sN Param.: 0.49 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
piperidine (in water)![]() ![]() |
water | N Param.: 18.13 sN Param.: 0.44 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
morpholine (in water)![]() ![]() |
water | N Param.: 15.62 sN Param.: 0.54 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
piperazine (in water)![]() ![]() |
water | N Param.: 17.22 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
perhydroazepine (in water)![]() ![]() |
water | N Param.: 18.29 sN Param.: 0.46 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
glycinenitrile (in water)![]() ![]() |
water | N Param.: 10.80 sN Param.: 0.61 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ethanolamine (in water)![]() ![]() |
water | N Param.: 12.61 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ethylenediamine (in water)![]() ![]() |
water | N Param.: 13.28 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
propargylamine (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
allylamine (in water)![]() ![]() |
water | N Param.: 13.21 sN Param.: 0.54 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
benzylamine (in water)![]() ![]() |
water | N Param.: 13.44 sN Param.: 0.55 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in water)![]() ![]() |
water | N Param.: 12.99 sN Param.: 0.73 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
p-toluidine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.79 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
4-methoxyaniline (in water)![]() ![]() |
water | N Param.: 14.28 sN Param.: 0.68 | ![]() ![]() ![]() | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
diethanolamine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.61 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
N-methyl-glycinenitrile (in water)![]() ![]() |
water | N Param.: 13.50 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
methyl glycinate (in water)![]() ![]() |
water | N Param.: 12.08 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
glycineamide (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
1,3-diaminopropane (in water)![]() ![]() |
water | N Param.: 14.02 sN Param.: 0.54 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
glycine (anionic, in water)![]() ![]() |
water | N Param.: 13.51 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
alanine (anionic, in water)![]() ![]() |
water | N Param.: 13.01 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
valine (anionic, in water)![]() ![]() |
water | N Param.: 13.65 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
leucine (anionic, in water)![]() ![]() |
water | N Param.: 14.01 sN Param.: 0.52 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
phenylalanine (anionic, in water)![]() ![]() |
water | N Param.: 14.12 sN Param.: 0.53 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
proline (anionic, in water)![]() ![]() |
water | N Param.: 18.08 sN Param.: 0.50 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
serine (anionic, in water)![]() ![]() |
water | N Param.: 13.16 sN Param.: 0.55 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
threonine (anionic, in water)![]() ![]() |
water | N Param.: 12.69 sN Param.: 0.60 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
asparagine (anionic, in water)![]() ![]() |
water | N Param.: 13.03 sN Param.: 0.53 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glutamine (anionic, in water)![]() ![]() |
water | N Param.: 13.45 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
arginine (betaine, in water)![]() ![]() |
water | N Param.: 12.96 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
histidine (anionic, in water)![]() ![]() |
water | N Param.: 13.83 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
aspartate (dianionic, in water)![]() ![]() |
water | N Param.: 13.81 sN Param.: 0.53 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glutamate (dianionic, in water)![]() ![]() |
water | N Param.: 13.96 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
cysteine (dianionic, in water, S-nucleophile!)![]() ![]() |
water | N Param.: 23.43 sN Param.: 0.42 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
methionine (anionic, in water)![]() ![]() |
water | N Param.: 13.16 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
beta-alanine (anionic, in water)![]() ![]() |
water | N Param.: 13.26 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
gamma-aminobutyric acid (anionic, in water)![]() ![]() |
water | N Param.: 13.55 sN Param.: 0.56 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glycylglycine (anionic, in water)![]() ![]() |
water | N Param.: 12.91 sN Param.: 0.59 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glycylglycylglycine (anionic, in water)![]() ![]() |
water | N Param.: 12.26 sN Param.: 0.63 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
imidazole (in water)![]() ![]() |
water | N Param.: 9.63 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in water)![]() ![]() |
water | N Param.: 9.91 sN Param.: 0.55 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in water)![]() ![]() |
water | N Param.: 9.45 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-pyridone anion (in water)![]() ![]() |
water | N Param.: 12.47 sN Param.: 0.52 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in water)![]() ![]() |
water | N Param.: 14.76 sN Param.: 0.48 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-nitro-imidazole anion (in water)![]() ![]() |
water | N Param.: 11.37 sN Param.: 0.53 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-formyl-imidazole anion (in water)![]() ![]() |
water | N Param.: 11.07 sN Param.: 0.50 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzotriazole anion (in water)![]() ![]() |
water | N Param.: 11.52 sN Param.: 0.67 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
purine anion (in water)![]() ![]() |
water | N Param.: 11.00 sN Param.: 0.54 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
theophylline anion (in water)![]() ![]() |
water | N Param.: 10.06 sN Param.: 0.71 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
adenine anion (in water)![]() ![]() |
water | N Param.: 10.93 sN Param.: 0.62 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
guanine anion (in water)![]() ![]() |
water | N Param.: 11.63 sN Param.: 0.59 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
9-methyl guanine anion (in water)![]() ![]() |
water | N Param.: 10.77 sN Param.: 0.65 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
guanosine anion (in water)![]() ![]() |
water | N Param.: 12.09 sN Param.: 0.52 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
uracil anion (in water)![]() ![]() |
water | N Param.: 10.75 sN Param.: 0.53 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
thymine anion (in water)![]() ![]() |
water | N Param.: 11.17 sN Param.: 0.51 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
1-methyl uracil anion (in water)![]() ![]() |
water | N Param.: 8.54 sN Param.: 0.77 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
hydrazine (in water)![]() ![]() |
water | N Param.: 13.46 sN Param.: 0.57 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
methylhydrazine (in water)![]() ![]() |
water | N Param.: 17.23 sN Param.: 0.45 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
2-phenylethylamine (in water)![]() ![]() |
water | N Param.: 13.40 sN Param.: 0.57 | ![]() ![]() ![]() | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
4-(dimethylamino)pyridine (in THF)![]() ![]() |
THF | N Param.: 15.90 sN Param.: 0.66 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
DBU (in THF)![]() ![]() |
THF | N Param.: 16.12 sN Param.: 0.67 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
azide ion (in 91nPr9AN)![]() ![]() |
nPrOH-MeCN mix | N Param.: 16.70 sN Param.: 0.73 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.54 sN Param.: 0.82 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 45M55AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.01 sN Param.: 0.80 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
pyrrolidine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.97 sN Param.: 0.63 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
piperidine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.63 sN Param.: 0.64 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
morpholine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.40 sN Param.: 0.64 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
diethanolamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.71 sN Param.: 0.67 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
hydrazine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.47 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
2,2,2-trifluoroethylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 10.20 sN Param.: 0.92 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
imidazole (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 10.41 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
hydroxylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 12.23 sN Param.: 0.66 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
ethanolamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.23 sN Param.: 0.65 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
benzylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.46 sN Param.: 0.62 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
n-propylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.66 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
4-(dimethylamino)pyridine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.20 sN Param.: 0.67 | ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
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 |