N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
pyrrolidine (in water)	water	N Param.: 17.21 s_N Param.: 0.49	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
piperazine (in water)	water	N Param.: 17.22 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
methylhydrazine (in water)	water	N Param.: 17.23 s_N Param.: 0.45	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
(S)-pyrrolidin-2-ylmethanamine	MeCN	N Param.: 17.24 s_N 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 s_N Param.: 0.65	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
triethylamine (in CH2Cl2)	dichloromethane	N Param.: 17.30 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
piperidine (in MeCN)	MeCN	N Param.: 17.35 s_N 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 s_N Param.: 0.68	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-benzylpyrrolidine	MeCN	N Param.: 17.43 s_N 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 s_N Param.: 0.64	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877