N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(S)-2-(methoxymethyl)pyrrolidine  |
MeCN | N Param.: 16.50 sN Param.: 0.71 |  | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-(trifluoromethyl)pyrrolidine |
MeCN | N Param.: 11.34 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
methyl L-prolinate |
MeCN | N Param.: 14.75 sN Param.: 0.82 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethylpyrrolidine-2-carboxamide |
MeCN | N Param.: 17.61 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N-propylpyrrolidine-2-carboxamide |
MeCN | N Param.: 15.20 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione |
MeCN | N Param.: 15.90 sN Param.: 0.77 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole |
MeCN | N Param.: 15.32 sN Param.: 0.72 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole |
MeCN | N Param.: 15.55 sN Param.: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate |
MeCN | N Param.: 13.57 sN Param.: 0.53 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea |
MeCN | N Param.: 14.97 sN Param.: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea |
MeCN | N Param.: 17.50 sN Param.: 0.64 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-tritylpyrrolidine |
MeCN | N Param.: 9.16 sN Param.: 1.39 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine |
MeCN | N Param.: 12.03 sN Param.: 0.98 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-diphenyl(pyrrolidin-2-yl)methanol |
MeCN | N Param.: 16.18 sN Param.: 0.56 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(azidodiphenylmethyl)pyrrolidine |
MeCN | N Param.: 9.90 sN Param.: 1.22 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-(triphenylsilyl)pyrrolidine |
MeCN | N Param.: 14.00 sN Param.: 0.84 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one |
MeCN | N Param.: 6.04 sN Param.: 0.92 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one |
MeCN | N Param.: 5.44 sN Param.: 1.12 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one |
MeCN | N Param.: 8.76 sN Param.: 0.89 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one |
MeCN | N Param.: 7.39 sN Param.: 1.00 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
TCAP (in MeCN) |
MeCN | N Param.: 15.60 sN Param.: 0.68 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
4-pyrrolidinopyridine (in MeCN) |
MeCN | N Param.: 14.99 sN Param.: 0.69 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
pyridine (in MeCN) |
MeCN | N Param.: 13.60 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyridine (in MeCN) |
MeCN | N Param.: 10.98 sN Param.: 0.66 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,6-dimethylpyridine (in MeCN) |
MeCN | N Param.: 9.11 sN Param.: 0.69 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,4,6-trimethylpyridine (in MeCN) |
MeCN | N Param.: 9.39 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
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 |
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 |
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 |
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 |