N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
hydroxylamine (in MeCN)	MeCN	N Param.: 12.80 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
N-methylhydroxylamine (in MeCN)	MeCN	N Param.: 14.10 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
ammonia (in MeCN)	MeCN	N Param.: 11.39 s_N Param.: 0.69	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
methylamine (in MeCN)	MeCN	N Param.: 15.19 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
dimethylamine (in MeCN)	MeCN	N Param.: 17.96 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
trimethylamine (in MeCN)	MeCN	N Param.: 23.05 s_N Param.: 0.45	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 19.51 s_N Param.: 0.47	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 17.19 s_N Param.: 0.64	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4P+) (in MeCN)	MeCN	N Param.: 16.48 s_N Param.: 0.60	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4N+) (in MeCN)	MeCN	N Param.: 16.68 s_N Param.: 0.59	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 15.51 s_N Param.: 0.62	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-(morpholino)pyridine (in MeCN)	MeCN	N Param.: 14.80 s_N Param.: 0.63	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
3-bromo-4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 12.96 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-amino-3,5-dibromo-pyridine (in MeCN)	MeCN	N Param.: 11.11 s_N Param.: 0.75	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
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
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
azide ion (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.30 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in 91nPr9AN)	nPrOH-MeCN mix	N Param.: 16.70 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in 91iPr9AN)	iPrOH-MeCN mix	N Param.: 17.07 s_N Param.: 0.71	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in DMSO)	DMSO	N Param.: 20.50 s_N Param.: 0.59	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in 45M55AN)	MeOH-MeCN mix	N Param.: 15.01 s_N Param.: 0.80	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
triethylamine (in MeCN)	MeCN	N Param.: 17.10 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
triethylamine (in CH2Cl2)	dichloromethane	N Param.: 17.30 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-pyrrolidine (in MeCN)	MeCN	N Param.: 20.59 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-pyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 20.60 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-piperidine (in MeCN)	MeCN	N Param.: 18.72 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-piperidine (in CH2Cl2)	dichloromethane	N Param.: 18.90 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-morpholine (in MeCN)	MeCN	N Param.: 16.80 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-morpholine (in CH2Cl2)	dichloromethane	N Param.: 16.50 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
nicotine (in CH2Cl2)	dichloromethane	N Param.: 10.40 s_N Param.: 1.04	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
nicotine (in MeCN)	MeCN	N Param.: 11.60 s_N Param.: 0.81	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
3-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 10.90 s_N Param.: 0.93	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
3-methylpyridine (in MeCN)	MeCN	N Param.: 11.50 s_N Param.: 0.80	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
1-methyl-2-phenylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 16.80 s_N Param.: 0.49	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
1-methyl-2-phenylpyrrolidine (in MeCN)	MeCN	N Param.: 15.70 s_N Param.: 0.54	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
alanine (anionic, in water)	water	N Param.: 13.01 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
valine (anionic, in water)	water	N Param.: 13.65 s_N Param.: 0.57	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
leucine (anionic, in water)	water	N Param.: 14.01 s_N Param.: 0.52	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
phenylalanine (anionic, in water)	water	N Param.: 14.12 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
proline (anionic, in water)	water	N Param.: 18.08 s_N Param.: 0.50	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
serine (anionic, in water)	water	N Param.: 13.16 s_N Param.: 0.55	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
threonine (anionic, in water)	water	N Param.: 12.69 s_N Param.: 0.60	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
asparagine (anionic, in water)	water	N Param.: 13.03 s_N Param.: 0.53	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
arginine (betaine, in water)	water	N Param.: 12.96 s_N Param.: 0.57	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
aspartate (dianionic, in water)	water	N Param.: 13.81 s_N Param.: 0.53	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
cysteine (dianionic, in water, S-nucleophile!)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h