Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
allylamine (in MeCN)	MeCN	N Param.: 14.37 s_N Param.: 0.66	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
2-benzyl-1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 14.36 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
triphenylphosphane	dichloromethane	N Param.: 14.33 s_N Param.: 0.65	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
anion of 3-methyl acetylacetone (in water)	water	N Param.: 14.33 s_N Param.: 0.69	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
peroxy-GABA	water	N Param.: 14.33 s_N Param.: 0.57	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
p-nitrophenolate (in DMSO)	DMSO	N Param.: 14.32 s_N Param.: 0.77	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
ethyl glycinate (in DMSO)	DMSO	N Param.: 14.30 s_N Param.: 0.67	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
p-methylphenolate (in H2O)	water	N Param.: 14.30 s_N Param.: 0.55	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
benzylamine (in MeCN)	MeCN	N Param.: 14.29 s_N Param.: 0.67	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
t-butylperoxy anion (in H2O)	water	N Param.: 14.29 s_N Param.: 0.51	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
4-methoxyaniline (in water)	water	N Param.: 14.28 s_N Param.: 0.68	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
Se-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.27 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
tris(2-methoxyphenyl)phosphane	dichloromethane	N Param.: 14.26 s_N Param.: 0.73	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
anion of (3-nitrophenyl)nitromethane (in water)	water	N Param.: 14.25 s_N Param.: 0.46	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
2-thiobarbiturate anion (in DMSO)	DMSO	N Param.: 14.24 s_N Param.: 0.82	J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223
2-Bz super-dmap (in MeCN)	MeCN	N Param.: 14.19 s_N Param.: 0.67	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
Se-HyperBTM (in THF)	THF	N Param.: 14.19 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
[H-B(2,4,6-F3C6H2)3]- [NEt4]+	MeCN	N Param.: 14.13 s_N Param.: 0.61	Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298
phenylalanine (anionic, in water)	water	N Param.: 14.12 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925