N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate	MeCN	N Param.: 13.57 s_N Param.: 0.53	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 13.58 s_N Param.: 0.77	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
cyanate (in MeCN)	MeCN	N Param.: 13.60 s_N Param.: 0.84	Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314
pyridine (in MeCN)	MeCN	N Param.: 13.60 s_N Param.: 0.60	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
valine (anionic, in water)	water	N Param.: 13.65 s_N Param.: 0.57	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
4-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 13.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-methoxypyridine (in CH2Cl2)	dichloromethane	N Param.: 13.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
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
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
aspartate (dianionic, in water)	water	N Param.: 13.81 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
histidine (anionic, in water)	water	N Param.: 13.83 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
methylamine (in water)	water	N Param.: 13.85 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
tetramisole (TM) (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
glutamate (dianionic, in water)	water	N Param.: 13.96 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
2,2-dimethylpyrrolidine	MeCN	N Param.: 13.96 s_N Param.: 0.76	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine	dichloromethane	N Param.: 14.00 s_N Param.: 0.70	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2-(triphenylsilyl)pyrrolidine	MeCN	N Param.: 14.00 s_N Param.: 0.84	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
leucine (anionic, in water)	water	N Param.: 14.01 s_N Param.: 0.52	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
1,3-diaminopropane (in water)	water	N Param.: 14.02 s_N Param.: 0.54	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine	dichloromethane	N Param.: 14.10 s_N Param.: 0.82	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
N-methylhydroxylamine (in MeCN)	MeCN	N Param.: 14.10 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
phenylalanine (anionic, in water)	water	N Param.: 14.12 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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, 64, e202514865 10.1002/anie.202514865
Se-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.27 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
4-methoxyaniline (in water)	water	N Param.: 14.28 s_N Param.: 0.68	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
benzylamine (in MeCN)	MeCN	N Param.: 14.29 s_N Param.: 0.67	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
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
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
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-aminobutan-1-ol (in DMSO)	DMSO	N Param.: 14.39 s_N Param.: 0.67	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
Se-HBTM (in CH2Cl2)	dichloromethane	N Param.: 14.42 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)	dichloromethane	N Param.: 14.43 s_N Param.: 0.81	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)	MeCN	N Param.: 14.43 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)	dichloromethane	N Param.: 14.44 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)	dichloromethane	N Param.: 14.45 s_N Param.: 0.78	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
7-PivO-HyperBTM	dichloromethane	N Param.: 14.49 s_N Param.: 0.66	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
azide ion (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.54 s_N Param.: 0.82	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine	dichloromethane	N Param.: 14.57 s_N Param.: 0.75	Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)	DMSO	N Param.: 14.58 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
4-(morpholino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 14.59 s_N Param.: 0.69	Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.72	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
Te-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865