N-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
hydroxylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.80 sN Param.: 0.63 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
N-methylhydroxylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.10 sN Param.: 0.76 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
ammonia (in MeCN)![]() ![]() |
MeCN | N Param.: 11.39 sN Param.: 0.69 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
methylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 15.19 sN Param.: 0.68 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
dimethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.96 sN Param.: 0.63 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
trimethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 23.05 sN Param.: 0.45 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 19.51 sN Param.: 0.47 | ![]() ![]() ![]() | J. Org. Chem. 2025, xx, ASAPArticle 10.1021/acs.joc.4c02668 |
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 |
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 |
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 |
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 |
2,2,2-trifluoroethylamine (in DMSO)![]() ![]() |
DMSO | N Param.: 12.15 sN Param.: 0.65 | ![]() ![]() ![]() | 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 |
ethyl glycinate (in DMSO)![]() ![]() |
DMSO | N Param.: 14.30 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
n-propylamine (in DMSO)![]() ![]() |
DMSO | N Param.: 15.70 sN Param.: 0.64 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
morpholine (in DMSO)![]() ![]() |
DMSO | N Param.: 16.96 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
piperidine (in DMSO)![]() ![]() |
DMSO | N Param.: 17.19 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 12.13 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
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 |
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 |
acetonitrile (in MeCN)![]() ![]() |
MeCN | N Param.: 2.23 sN Param.: 0.84 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
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-methylpyrrolidine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.78 sN Param.: 0.71 | ![]() ![]() ![]() | 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 |
(R)-2-isopropylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.44 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,2-dimethylpyrrolidine![]() ![]() |
MeCN | N Param.: 13.96 sN Param.: 0.76 | ![]() ![]() ![]() | 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)-2-benzhydrylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.61 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(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 |
(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 |
(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 |
(S)-2-(azidomethyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 15.43 sN Param.: 0.73 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(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 |
(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 |