N-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
2-aminobutan-1-ol (in DMSO)   |
DMSO | N Param.: 14.39 sN Param.: 0.67 |
 |
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
benzylamine (in DMSO)  |
DMSO | N Param.: 15.28 sN Param.: 0.65 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
1-aminopropan-2-ol (in DMSO)  |
DMSO | N Param.: 15.47 sN Param.: 0.65 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
diethanolamine (in DMSO)  |
DMSO | N Param.: 15.51 sN Param.: 0.70 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
ethanolamine (in DMSO)  |
DMSO | N Param.: 16.07 sN Param.: 0.61 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
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 |
quinine  |
dichloromethane | N Param.: 10.46 sN Param.: 0.75 |
|
J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
quinidine  |
dichloromethane | N Param.: 10.54 sN Param.: 0.74 |
|
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 |
imidazole (in DMSO)  |
DMSO | N Param.: 11.58 sN Param.: 0.79 |
|
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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 MeCN)  |
MeCN | N Param.: 11.90 sN Param.: 0.73 |
|
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 |
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 |
2-methyl-imidazole (in water)  |
water | N Param.: 9.45 sN Param.: 0.54 |
|
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 |
benzimidazole (in DMSO)  |
DMSO | N Param.: 10.50 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 |
2-methyl-benzimidazole (in DMSO)  |
DMSO | N Param.: 10.02 sN Param.: 0.85 |
|
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methyl-benzimidazole (in DMSO)  |
DMSO | N Param.: 10.69 sN Param.: 0.79 |
|
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2,5-dimethyl-benzimidazole (in DMSO)  |
DMSO | N Param.: 10.21 sN Param.: 0.85 |
|
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5,6-dimethyl-benzimidazole (in DMSO)  |
DMSO | N Param.: 11.08 sN Param.: 0.71 |
|
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methoxy-benzimidazole (in DMSO)  |
DMSO | N Param.: 11.00 sN Param.: 0.71 |
|
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 |
triethylamine (in CH2Cl2)  |
dichloromethane | N Param.: 17.30 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-pyrrolidine (in CH2Cl2)  |
dichloromethane | N Param.: 20.60 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-piperidine (in CH2Cl2)  |
dichloromethane | N Param.: 18.90 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 |
N-methyl-morpholine (in CH2Cl2)  |
dichloromethane | N Param.: 16.50 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
phthalimide anion (in DMSO)  |
DMSO | N Param.: 15.52 sN Param.: 0.67 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
succinimide anion (in DMSO)  |
DMSO | N Param.: 16.03 sN Param.: 0.66 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
maleimide anion (in DMSO)  |
DMSO | N Param.: 14.87 sN Param.: 0.76 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
trifluoroacetamide anion (in DMSO)  |
DMSO | N Param.: 15.81 sN Param.: 0.64 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
N-methyl-trifluoroacetamide anion (in DMSO)  |
DMSO | N Param.: 15.70 sN Param.: 0.71 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
4,4-dimethyl-glutarimide anion (in DMSO)  |
DMSO | N Param.: 17.52 sN Param.: 0.63 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
diacetamide anion (in DMSO)  |
DMSO | N Param.: 16.05 sN Param.: 0.70 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
cyanamide anion (in DMSO)  |
DMSO | N Param.: 20.33 sN Param.: 0.64 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
p-toluenesulfonamide anion (in DMSO)  |
DMSO | N Param.: 17.14 sN Param.: 0.60 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
methanesulfonamide anion (in DMSO)  |
DMSO | N Param.: 18.61 sN Param.: 0.53 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
hydantoin anion (in DMSO)  |
DMSO | N Param.: 17.52 sN Param.: 0.55 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
1,3-oxazolidin-2-one anion (in DMSO)  |
DMSO | N Param.: 22.40 sN Param.: 0.59 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)  |
DMSO | N Param.: 22.67 sN Param.: 0.54 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
ethyl N-acetylcarbamate anion (in DMSO)  |
DMSO | N Param.: 15.99 sN Param.: 0.70 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
2-pyridone anion (in DMSO)  |
DMSO | N Param.: 19.91 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
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 |
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 DMSO)  |
DMSO | N Param.: 18.97 sN Param.: 0.62 |
|
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 |
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 |
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 |
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine  |
dichloromethane | N Param.: 13.00 sN Param.: 0.83 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole  |
dichloromethane | N Param.: 12.98 sN Param.: 0.81 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole  |
dichloromethane | N Param.: 13.42 sN Param.: 0.73 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine  |
dichloromethane | N Param.: 14.10 sN Param.: 0.82 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)  |
dichloromethane | N Param.: 14.45 sN Param.: 0.78 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
HyperBTM (in CH2Cl2)  |
dichloromethane | N Param.: 14.96 sN Param.: 0.64 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine  |
dichloromethane | N Param.: 15.30 sN Param.: 0.55 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine  |
dichloromethane | N Param.: 16.50 sN Param.: 0.48 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine  |
dichloromethane | N Param.: 12.95 sN Param.: 0.58 |
|
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
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 |
imidazole anion (in DMSO)  |
DMSO | N Param.: 21.09 sN Param.: 0.51 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-methyl-imidazole anion (in DMSO)  |
DMSO | N Param.: 21.03 sN Param.: 0.50 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-methyl-imidazole anion (in DMSO)  |
DMSO | N Param.: 21.29 sN Param.: 0.51 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2,4-dimethyl-imidazole anion (in DMSO)  |
DMSO | N Param.: 20.69 sN Param.: 0.60 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-nitro-imidazole anion (in DMSO)  |
DMSO | N Param.: 14.81 sN Param.: 0.71 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-formyl-imidazole anion (in DMSO)  |
DMSO | N Param.: 16.06 sN Param.: 0.68 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |