N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
diacetamide anion (in DMSO)	DMSO	N Param.: 16.05 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
diethanolamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.71 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
diethanolamine (in DMSO)	DMSO	N Param.: 15.51 s_N Param.: 0.70	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
diethanolamine (in water)	water	N Param.: 13.00 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
diethylamine (in water)	water	N Param.: 14.68 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
dimethylamine (in MeCN)	MeCN	N Param.: 17.96 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
dimethylamine (in water)	water	N Param.: 17.12 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
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
ethanolamine (in DMSO)	DMSO	N Param.: 16.07 s_N Param.: 0.61	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
ethanolamine (in water)	water	N Param.: 12.61 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
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
ethyl N-acetylcarbamate anion (in DMSO)	DMSO	N Param.: 15.99 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
ethylamine (in water)	water	N Param.: 12.87 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethylenediamine (in water)	water	N Param.: 13.28 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
formohydrazide (in MeCN)	MeCN	N Param.: 10.35 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
gamma-aminobutyric acid (anionic, in water)	water	N Param.: 13.55 s_N Param.: 0.56	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glutamate (dianionic, in water)	water	N Param.: 13.96 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glutamine (anionic, in water)	water	N Param.: 13.45 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycineamide (in water)	water	N Param.: 12.29 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycinenitrile (in water)	water	N Param.: 10.80 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycylglycine (anionic, in water)	water	N Param.: 12.91 s_N Param.: 0.59	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycylglycylglycine (anionic, in water)	water	N Param.: 12.26 s_N Param.: 0.63	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
guanine anion (in water)	water	N Param.: 11.63 s_N Param.: 0.59	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
guanosine anion (in water)	water	N Param.: 12.09 s_N Param.: 0.52	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
HBTM (in CH2Cl2)	dichloromethane	N Param.: 13.45 s_N Param.: 0.72	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
histidine (anionic, in water)	water	N Param.: 13.83 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
hydantoin anion (in DMSO)	DMSO	N Param.: 17.52 s_N Param.: 0.55	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
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
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
hydrazine (in water)	water	N Param.: 13.46 s_N Param.: 0.57	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
hydroxylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.23 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
hydroxylamine (in MeCN)	MeCN	N Param.: 12.80 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
hydroxylamine (in water)	water	N Param.: 11.41 s_N Param.: 0.55	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.96 s_N Param.: 0.64	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
HyperNTM	dichloromethane	N Param.: 14.47 s_N Param.: 0.72	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
HyperPTM	dichloromethane	N Param.: 13.43 s_N Param.: 0.79	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
imidazole (in 91M9AN)	MeOH-MeCN mix	N Param.: 10.41 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
imidazole (in DMSO)	DMSO	N Param.: 11.58 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
imidazole (in MeCN)	MeCN	N Param.: 11.47 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
imidazole (in water)	water	N Param.: 9.63 s_N Param.: 0.57	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
imidazole anion (in DMSO)	DMSO	N Param.: 21.09 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
isopropylamine (in water)	water	N Param.: 12.00 s_N Param.: 0.56	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
leucine (anionic, in water)	water	N Param.: 14.01 s_N Param.: 0.52	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
maleimide anion (in DMSO)	DMSO	N Param.: 14.87 s_N Param.: 0.76	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
methanesulfonamide anion (in DMSO)	DMSO	N Param.: 18.61 s_N Param.: 0.53	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883