Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
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
methionine (anionic, in water)	water	N Param.: 13.16 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
beta-alanine (anionic, in water)	water	N Param.: 13.26 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
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
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO)	DMSO	N Param.: 18.50 s_N Param.: 0.75	Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO)	DMSO	N Param.: 22.60 s_N Param.: 0.57	Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO)	DMSO	N Param.: 24.30 s_N Param.: 0.51	Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h
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 DMSO)	DMSO	N Param.: 11.58 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
1-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.90 s_N Param.: 0.73	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-imidazole (in water)	water	N Param.: 9.91 s_N Param.: 0.55	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-phenyl-imidazole (in MeCN)	MeCN	N Param.: 11.31 s_N Param.: 0.67	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.74 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-imidazole (in water)	water	N Param.: 9.45 s_N Param.: 0.54	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
4-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.79 s_N Param.: 0.77	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2,4-dimethyl-imidazole (in MeCN)	MeCN	N Param.: 11.51 s_N Param.: 0.84	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-(trimethylsilyl)-imidazole (in MeCN)	MeCN	N Param.: 11.43 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
benzimidazole (in DMSO)	DMSO	N Param.: 10.50 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-benzimidazole (in MeCN)	MeCN	N Param.: 10.37 s_N Param.: 0.82	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.02 s_N Param.: 0.85	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
5-methyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.69 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2,5-dimethyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.21 s_N Param.: 0.85	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
5,6-dimethyl-benzimidazole (in DMSO)	DMSO	N Param.: 11.08 s_N Param.: 0.71	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
5-methoxy-benzimidazole (in DMSO)	DMSO	N Param.: 11.00 s_N Param.: 0.71	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
benzotriazole (in MeCN)	MeCN	N Param.: 7.69 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-benzotriazole (in MeCN)	MeCN	N Param.: 7.77 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
thioacetate (in MeCN)	MeCN	N Param.: 21.20 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-ethyl dithiocarbonate (in MeCN)	MeCN	N Param.: 19.30 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-isopropyl dithiocarbonate (in MeCN)	MeCN	N Param.: 18.27 s_N Param.: 0.78	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
N,N-dimethyl dithiocarbamate (in MeCN)	MeCN	N Param.: 20.93 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
pyrrolidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 22.40 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
piperidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.84 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
4-methylpiperazin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.61 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
morpholin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 21.72 s_N Param.: 0.64	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
cyanoborate ion (in water)	water	N Param.: 9.99 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
cysteine (dianionic, in water)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
NADPH (in water)	water	N Param.: 10.68 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
NADH (in water)	water	N Param.: 10.37 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
allyltris(trimethylsilyl)silane	dichloromethane	N Param.: 1.95 s_N Param.: 0.98	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(2-methylallyl)tris(trimethylsilyl)silane	dichloromethane	N Param.: 4.63 s_N Param.: 0.87	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
2-(tris(trimethylsilyl)siloxy)propene	dichloromethane	N Param.: 6.04 s_N Param.: 0.82	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
1-(tris(trimethylsilyl)siloxy)cyclohexene	dichloromethane	N Param.: 5.07 s_N Param.: 0.91	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(tris(trimethylsilyl)siloxy)ethene	dichloromethane	N Param.: 4.01 s_N Param.: 0.83	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
2-Me super-dmap (in MeCN)	MeCN	N Param.: 16.65 s_N Param.: 0.58	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Et super-dmap (in MeCN)	MeCN	N Param.: 16.81 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Bn super-dmap (in MeCN)	MeCN	N Param.: 17.69 s_N Param.: 0.57	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Ac super-dmap (in MeCN)	MeCN	N Param.: 15.39 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
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
dipp Imd boronate	dichloromethane	N Param.: 9.55 s_N Param.: 0.81	Org. Lett. 2012, 14, 82-85 10.1021/ol202836p
Me2 Imd boronate	dichloromethane	N Param.: 11.88 s_N Param.: 0.71	Org. Lett. 2012, 14, 82-85 10.1021/ol202836p
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 1.47 s_N Param.: 0.89	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
3,3,3-trifluoro-2-(trimethylsiloxy)propene	dichloromethane	N Param.: -2.94 s_N Param.: 1.11	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene	dichloromethane	N Param.: -3.52 s_N Param.: 1.17	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.92 s_N Param.: 0.70	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 10.97 s_N Param.: 0.63	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.15 s_N Param.: 0.77	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.56 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.46 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 6.30 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 6.63 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.72 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.68 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)	MeCN	N Param.: 11.29 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 21.50 s_N Param.: 0.45	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 16.54 s_N Param.: 0.47	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 20.41 s_N Param.: 0.46	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 23.00 s_N Param.: 0.46	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
hypochlorite (in water)	water	N Param.: 14.50 s_N Param.: 0.58	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
hypobromite (in water)	water	N Param.: 16.69 s_N Param.: 0.46	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
bromite (in water)	water	N Param.: 12.75 s_N Param.: 0.59	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
peroxomonosulfate (in water)	water	N Param.: 14.41 s_N Param.: 0.60	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]