N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
azide ion (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.30 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
1-methyl uracil anion (in DMSO)	DMSO	N Param.: 16.36 s_N Param.: 0.69	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 16.38 s_N Param.: 0.60	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
4-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.40 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
(R)-2-isopropylpyrrolidine	MeCN	N Param.: 16.44 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
hydrazine (in MeCN)	MeCN	N Param.: 16.45 s_N 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 s_N Param.: 0.60	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
N-methyl-morpholine (in CH2Cl2)	dichloromethane	N Param.: 16.50 s_N 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 s_N Param.: 0.48	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(S)-2-(methoxymethyl)pyrrolidine	MeCN	N Param.: 16.50 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877