N-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
pyrrolidine (in water)   |
water | N Param.: 17.21 sN Param.: 0.49 |
 |
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 |
methylhydrazine (in water)  |
water | N Param.: 17.23 sN Param.: 0.45 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
(S)-pyrrolidin-2-ylmethanamine  |
MeCN | N Param.: 17.24 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN)  |
MeCN | N Param.: 17.28 sN Param.: 0.65 |
|
J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
triethylamine (in CH2Cl2)  |
dichloromethane | N Param.: 17.30 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
piperidine (in MeCN)  |
MeCN | N Param.: 17.35 sN Param.: 0.68 |
|
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine  |
MeCN | N Param.: 17.41 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-benzylpyrrolidine  |
MeCN | N Param.: 17.43 sN Param.: 0.66 |
|
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 |
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 |
hydantoin anion (in DMSO)  |
DMSO | N Param.: 17.52 sN Param.: 0.55 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
(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 |
thymine anion (in DMSO)  |
DMSO | N Param.: 17.63 sN Param.: 0.62 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-Bn super-dmap (in MeCN)  |
MeCN | N Param.: 17.69 sN Param.: 0.57 |
|
Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
methylhydrazine (in MeCN)  |
MeCN | N Param.: 17.73 sN Param.: 0.58 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
trimethylhydrazine (in MeCN)  |
MeCN | N Param.: 17.75 sN Param.: 0.53 |
|
Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in CH2Cl2)  |
dichloromethane | N Param.: 17.88 sN Param.: 0.73 |
|
J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
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 |
dimethylamine (in MeCN)  |
MeCN | N Param.: 17.96 sN Param.: 0.63 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
adenine anion (in DMSO)  |
DMSO | N Param.: 18.00 sN Param.: 0.55 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
proline (anionic, in water)  |
water | N Param.: 18.08 sN Param.: 0.50 |
|
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
piperidine (in water)  |
water | N Param.: 18.13 sN Param.: 0.44 |
|
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 |
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine  |
MeCN | N Param.: 18.33 sN Param.: 0.64 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
pyrrolidine (inMeCN)  |
MeCN | N Param.: 18.58 sN Param.: 0.61 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
methanesulfonamide anion (in DMSO)  |
DMSO | N Param.: 18.61 sN Param.: 0.53 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
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 |
DABCO (in MeCN)  |
MeCN | N Param.: 18.80 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
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 |
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 |
benzimidazole anion (in DMSO)  |
DMSO | N Param.: 19.13 sN Param.: 0.55 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN)  |
MeCN | N Param.: 19.51 sN Param.: 0.47 |
|
J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in CH2Cl2)  |
dichloromethane | N Param.: 19.63 sN Param.: 0.65 |
|
J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
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 |
prolinate (in MeCN)  |
MeCN | N Param.: 19.95 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
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 |
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 |
cyanamide anion (in DMSO)  |
DMSO | N Param.: 20.33 sN Param.: 0.64 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
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 |
quinuclidine (in MeCN)  |
MeCN | N Param.: 20.54 sN Param.: 0.60 |
|
Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
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 |
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 |
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 |
imidazole anion (in DMSO)  |
DMSO | N Param.: 21.09 sN Param.: 0.51 |
|
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 |
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 |
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 |