N-Nucleophiles
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| Name | Solvent | Reactivity Parameters | Classification | Reference (title or year) | 
|---|---|---|---|---|
| pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN)   | MeCN | N Param.: 19.51sN 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.: 19.63sN Param.: 0.65 |    | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 | 
| 2-pyridone anion (in DMSO)   | DMSO | N Param.: 19.91sN Param.: 0.60 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| prolinate (in MeCN)   | MeCN | N Param.: 19.95sN Param.: 0.68 |    | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | 
| 2-pyridone anion (in MeCN)   | MeCN | N Param.: 20.11sN Param.: 0.57 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| 4-pyridone anion (in MeCN)   | MeCN | N Param.: 20.22sN Param.: 0.49 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| cyanamide anion (in DMSO)   | DMSO | N Param.: 20.33sN Param.: 0.64 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| azide ion (in DMSO)   | DMSO | N Param.: 20.50sN Param.: 0.59 |    | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | 
| quinuclidine (in MeCN)   | MeCN | N Param.: 20.54sN Param.: 0.60 |    | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 | 
| N-methyl-pyrrolidine (in MeCN)   | MeCN | N Param.: 20.59sN Param.: 0.52 |    | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| N-methyl-pyrrolidine (in CH2Cl2)   | dichloromethane | N Param.: 20.60sN 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.: 20.69sN Param.: 0.60 |    | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | 
| 2-methyl-imidazole anion (in DMSO)   | DMSO | N Param.: 21.03sN Param.: 0.50 |    | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | 
| imidazole anion (in DMSO)   | DMSO | N Param.: 21.09sN Param.: 0.51 |    | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | 
| 4-methyl-imidazole anion (in DMSO)   | DMSO | N Param.: 21.29sN 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.: 22.40sN Param.: 0.59 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| 1,1-dimethylhydrazine (in MeCN)   | MeCN | N Param.: 22.41sN Param.: 0.45 |    | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 | 
| (S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)   | DMSO | N Param.: 22.67sN Param.: 0.54 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| trimethylamine (in MeCN)   | MeCN | N Param.: 23.05sN Param.: 0.45 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| cysteine (dianionic, in water, S-nucleophile!)   | water | N Param.: 23.43sN Param.: 0.42 |    | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | 
