Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
4-(dimethylamino)pyridine (in H2O)	water	N Param.: 13.19 s_N Param.: 0.56	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
p-toluidine (in MeCN)	MeCN	N Param.: 13.19 s_N Param.: 0.69	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
4-(dimethylamino)pyridine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.20 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
fluoride (in 80% aq EtOH)	water-EtOH mix	N Param.: 13.20 s_N Param.: 0.53	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
allylamine (in water)	water	N Param.: 13.21 s_N Param.: 0.54	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
anion of (4-cyanophenyl)nitromethane (in water)	water	N Param.: 13.23 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
ethanolamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.23 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
di(methoxyethyl)amine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.93	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
4-acetamido-pyridine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
beta-alanine (anionic, in water)	water	N Param.: 13.26 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
ethylenediamine (in water)	water	N Param.: 13.28 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
chloride (in 80% aq MeCN)	water-MeCN mix	N Param.: 13.30 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
tetrahydrothiophene (in MeCN)	MeCN	N Param.: 13.30 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
IU3	dichloromethane	N Param.: 13.31 s_N Param.: 0.69	Angew. Chem. Int. Ed. 2025, , in print 10.1002/anie.202514865
n-propylamine (in water)	water	N Param.: 13.33 s_N Param.: 0.56	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
1-(N-piperidino)cyclohexene	dichloromethane	N Param.: 13.36 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
triisopropylphosphane	dichloromethane	N Param.: 13.37 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
2-phenylethylamine (in water)	water	N Param.: 13.40 s_N Param.: 0.57	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
1-(N-morpholino)cyclopentene	dichloromethane	N Param.: 13.41 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
anion of nitroethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.41 s_N Param.: 0.67	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769