N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
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 |
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 |
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 |
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 |
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2) |
dichloromethane | N Param.: 19.31 sN Param.: 0.46 | | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 |
N-methylenepyrrolidin-1-amine (in CH2Cl2) |
dichloromethane | N Param.: 17.90 sN Param.: 0.48 | | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 |
(S)-3,3-difluoro-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine (in CH2Cl2) |
dichloromethane | N Param.: 10.83 sN Param.: 0.80 | | ARKIVOC 2024, (4), 202312093 10.24820/ark.5550190[...] |
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 |
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 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 |
cyanate (in MeCN) |
MeCN | N Param.: 13.60 sN Param.: 0.84 | | Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 |
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 |
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 |
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 |
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 |
1,1,3,3-tetramethylguanidine |
dichloromethane | N Param.: 13.58 sN Param.: 0.77 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
2-benzyl-1,1,3,3-tetramethylguanidine |
dichloromethane | N Param.: 14.36 sN Param.: 0.79 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
1,3-dimethylimidazolidin-2-imine |
dichloromethane | N Param.: 12.46 sN Param.: 0.87 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine |
dichloromethane | N Param.: 14.00 sN Param.: 0.70 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO) |
dichloromethane | N Param.: 14.44 sN Param.: 0.79 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN) |
dichloromethane | N Param.: 16.15 sN Param.: 0.73 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD) |
dichloromethane | N Param.: 14.43 sN Param.: 0.81 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine |
dichloromethane | N Param.: 16.16 sN Param.: 0.75 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
DBN (in CH2Cl2) |
dichloromethane | N Param.: 15.50 sN Param.: 0.76 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
4-methoxyaniline (in water) |
water | N Param.: 14.28 sN Param.: 0.68 | | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
2-phenylethylamine (in water) |
water | N Param.: 13.40 sN Param.: 0.57 | | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
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 |
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2) |
dichloromethane | N Param.: 12.92 sN Param.: 0.77 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2) |
dichloromethane | N Param.: 12.31 sN Param.: 0.77 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2) |
dichloromethane | N Param.: 10.03 sN Param.: 0.75 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |