Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
N-methyl-glycinenitrile (in water)	water	N Param.: 13.50 s_N Param.: 0.59	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
9-MeS-HyperBTM	dichloromethane	N Param.: 13.49 s_N Param.: 0.78	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
hydrazine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.47 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
benzylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.46 s_N Param.: 0.62	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
hydrazine (in water)	water	N Param.: 13.46 s_N Param.: 0.57	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
1,3-di-tert-butyl-1,3,2-diazaphosphinane (in MeCN)	MeCN	N Param.: 13.46 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456
7-F-BTM (in CH2Cl2)	dichloromethane	N Param.: 13.46 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
glutamine (anionic, in water)	water	N Param.: 13.45 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
HBTM (in CH2Cl2)	dichloromethane	N Param.: 13.45 s_N Param.: 0.72	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
benzylamine (in water)	water	N Param.: 13.44 s_N Param.: 0.55	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
HyperPTM	dichloromethane	N Param.: 13.43 s_N Param.: 0.79	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
4-methoxyaniline (in MeCN)	MeCN	N Param.: 13.42 s_N Param.: 0.73	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole	dichloromethane	N Param.: 13.42 s_N Param.: 0.73	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
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
n-propylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.41 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
2-phenylethylamine (in water)	water	N Param.: 13.40 s_N Param.: 0.57	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
triisopropylphosphane	dichloromethane	N Param.: 13.37 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
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