N-Nucleophiles
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| 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 |
2,2,2-trifluoroethylamine (in DMSO) |
DMSO | N Param.: 12.15 sN Param.: 0.65 | | 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 |
ethyl glycinate (in DMSO) |
DMSO | N Param.: 14.30 sN Param.: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
n-propylamine (in DMSO) |
DMSO | N Param.: 15.70 sN Param.: 0.64 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
morpholine (in DMSO) |
DMSO | N Param.: 16.96 sN Param.: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
piperidine (in DMSO) |
DMSO | N Param.: 17.19 sN Param.: 0.71 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
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 |
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 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 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 91iPr9AN) |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in DMSO) |
DMSO | N Param.: 20.50 sN Param.: 0.59 | | 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-chloropyridine (in CH2Cl2) |
dichloromethane | N Param.: 11.70 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
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 CH2Cl2) |
dichloromethane | N Param.: 12.90 sN Param.: 0.67 | | 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 CH2Cl2) |
dichloromethane | N Param.: 13.70 sN Param.: 0.67 | | 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 CH2Cl2) |
dichloromethane | N Param.: 13.70 sN Param.: 0.67 | | 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 CH2Cl2) |
dichloromethane | N Param.: 15.20 sN Param.: 0.67 | | 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 CH2Cl2) |
dichloromethane | N Param.: 15.80 sN Param.: 0.66 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
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-(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-(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 |
4-(dimethylamino)pyridine (in DMSO) |
DMSO | N Param.: 14.80 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-(dimethylamino)pyridine (in DMF) |
DMF | N Param.: 14.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-pyrrolidinopyridine (in CH2Cl2) |
dichloromethane | N Param.: 15.90 sN Param.: 0.67 | | 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 |
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 water) |
water | N Param.: 12.99 sN Param.: 0.73 | | 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 water) |
water | N Param.: 13.00 sN Param.: 0.79 | | 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 water) |
water | N Param.: 14.28 sN Param.: 0.68 | | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
4-methoxyaniline (in MeCN) |
MeCN | N Param.: 13.42 sN Param.: 0.73 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
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 |
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 |
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 |
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 |