N-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
(R)-2-isopropylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.44 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
hydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.45 sN Param.: 0.56 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.48 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2025, xx, ASAPArticle 10.1021/acs.joc.4c02668 |
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 |
(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 |
(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 |
(S)-2-benzhydrylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.61 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-Me super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.65 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4N+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.68 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2025, xx, ASAPArticle 10.1021/acs.joc.4c02668 |
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 |
(S)-pyrrolidin-2-ylmethanol![]() ![]() |
MeCN | N Param.: 16.74 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-methylpyrrolidine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.78 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
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 |
1-methyl-2-phenylpyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 16.80 sN Param.: 0.49 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
2-Et super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.81 sN Param.: 0.60 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
morpholine (in DMSO)![]() ![]() |
DMSO | N Param.: 16.96 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
uracil anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.04 sN Param.: 0.63 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
triethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.10 sN Param.: 0.52 | ![]() | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
dimethylamine (in water)![]() ![]() |
water | N Param.: 17.12 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
p-toluenesulfonamide anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.14 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
piperidine (in DMSO)![]() ![]() |
DMSO | N Param.: 17.19 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 17.19 sN Param.: 0.64 | ![]() ![]() ![]() | J. Org. Chem. 2025, xx, ASAPArticle 10.1021/acs.joc.4c02668 |
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 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, xx, ASAPArticle 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, xx, ASAPArticle 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 |