Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)	THF	N Param.: 18.68 s_N Param.: 0.63	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)	THF	N Param.: 17.80 s_N Param.: 0.79	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole	THF	N Param.: 19.84 s_N Param.: 0.58	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
4-methylthiophenolate (in DMSO)	DMSO	N Param.: 24.35 s_N Param.: 0.69	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
naphthalene-2-thiolate (in DMSO)	DMSO	N Param.: 22.55 s_N Param.: 0.83	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
4-methoxythiophenolate (in DMSO)	DMSO	N Param.: 24.97 s_N Param.: 0.68	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
enolate of 3-isochromanone (in DMSO)	DMSO	N Param.: 25.39 s_N Param.: 0.54	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
enolate of 2-coumaranone (in DMSO)	DMSO	N Param.: 19.60 s_N Param.: 0.75	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
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
50% water/50% HFIP (w/w)	water-HFIP mix	N Param.: 1.50 s_N Param.: 1.03	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
30% water/70% HFIP (w/w)	water-HFIP mix	N Param.: 1.65 s_N Param.: 0.96	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
10% water/90% HFIP (w/w)	water-HFIP mix	N Param.: 0.96 s_N Param.: 0.93	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
7% water/93% HFIP (w/w)	water-HFIP mix	N Param.: 0.34 s_N Param.: 0.96	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
5% water/95% HFIP (w/w)	water-HFIP mix	N Param.: -0.10 s_N Param.: 0.97	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
3% water/97% HFIP (w/w)	water-HFIP mix	N Param.: -1.19 s_N Param.: 1.08	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
2% water/98% HFIP (w/w)	water-HFIP mix	N Param.: -1.62 s_N Param.: 1.10	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
1% water/99% HFIP (w/w)	water-HFIP mix	N Param.: -1.93 s_N Param.: 1.09	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
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
N-vinylcarbazole	dichloromethane	N Param.: 5.02 s_N Param.: 0.94	Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l
2,4,6-trimethylstyrene	dichloromethane	N Param.: 0.68 s_N Param.: 1.09	Macromolecules 2005, 38, 33-40 10.1021/ma048389o
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