N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
piperidine (in water)	water	N Param.: 18.13 s_N Param.: 0.44	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
proline (anionic, in water)	water	N Param.: 18.08 s_N Param.: 0.50	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
adenine anion (in DMSO)	DMSO	N Param.: 18.00 s_N Param.: 0.55	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
dimethylamine (in MeCN)	MeCN	N Param.: 17.96 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
N-methylenepyrrolidin-1-amine (in CH2Cl2)	dichloromethane	N Param.: 17.90 s_N Param.: 0.48	Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in CH2Cl2)	dichloromethane	N Param.: 17.88 s_N Param.: 0.73	J. Am. Chem. Soc. 2025, xx, ASAPArticle 10.1021/jacs.4c14825
trimethylhydrazine (in MeCN)	MeCN	N Param.: 17.75 s_N Param.: 0.53	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
methylhydrazine (in MeCN)	MeCN	N Param.: 17.73 s_N Param.: 0.58	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
2-Bn super-dmap (in MeCN)	MeCN	N Param.: 17.69 s_N Param.: 0.57	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
thymine anion (in DMSO)	DMSO	N Param.: 17.63 s_N Param.: 0.62	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411