Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
N-methyl-1-phenylmethanimine (in CH2Cl2)  |
dichloromethane | N Param.: 8.60 sN Param.: 0.77 |  | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 |
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2) |
dichloromethane | N Param.: 7.90 sN Param.: 0.76 | | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 |
N-phenylpropan-2-imine (in CH2Cl2) |
dichloromethane | N Param.: 9.53 sN Param.: 0.85 | | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 |
N-(phenylmethyl)propan-2-imine (in CH2Cl2) |
dichloromethane | N Param.: 11.13 sN Param.: 0.73 | | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 |
N-phenylcyclohexanimine (in CH2Cl2) |
dichloromethane | N Param.: 8.80 sN Param.: 1.00 | | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 |
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) |
DMSO | N Param.: 26.95 sN Param.: 0.52 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO) |
DMSO | N Param.: 27.77 sN Param.: 0.47 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) |
DMSO | N Param.: 29.10 sN Param.: 0.50 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) |
DMSO | N Param.: 29.02 sN Param.: 0.49 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO) |
DMSO | N Param.: 30.82 sN Param.: 0.41 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
cyano((diphenylmethylene)amino)methanide |
DMSO | N Param.: 29.50 sN Param.: 0.50 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN) |
MeCN | N Param.: 3.00 sN Param.: 0.83 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN) |
MeCN | N Param.: 5.18 sN Param.: 0.94 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
3-(trimethylsiloxy)-1H-indene (in MeCN) |
MeCN | N Param.: 7.32 sN Param.: 0.82 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN) |
MeCN | N Param.: 5.06 sN Param.: 0.91 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
3-pyrrolidino-1H-indene (in MeCN) |
MeCN | N Param.: 15.27 sN Param.: 0.93 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN) |
MeCN | N Param.: 14.09 sN Param.: 0.66 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
diazocyclopentadiene (in CH2Cl2) |
dichloromethane | N Param.: 4.84 sN Param.: 1.06 | | Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327 |
pyridine (in MeCN) |
MeCN | N Param.: 13.60 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 10.52 sN Param.: 0.78 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyridine (in MeCN) |
MeCN | N Param.: 10.98 sN Param.: 0.66 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,6-dimethylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 9.87 sN Param.: 0.68 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,6-dimethylpyridine (in MeCN) |
MeCN | N Param.: 9.11 sN Param.: 0.69 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,4,6-trimethylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 9.34 sN Param.: 0.71 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,4,6-trimethylpyridine (in MeCN) |
MeCN | N Param.: 9.39 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
allyltris(trimethylsilyl)silane |
dichloromethane | N Param.: 1.95 sN Param.: 0.98 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
(2-methylallyl)tris(trimethylsilyl)silane |
dichloromethane | N Param.: 4.63 sN Param.: 0.87 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
2-(tris(trimethylsilyl)siloxy)propene |
dichloromethane | N Param.: 6.04 sN Param.: 0.82 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
1-(tris(trimethylsilyl)siloxy)cyclohexene |
dichloromethane | N Param.: 5.07 sN Param.: 0.91 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
(tris(trimethylsilyl)siloxy)ethene |
dichloromethane | N Param.: 4.01 sN Param.: 0.83 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
2-Me super-dmap (in MeCN) |
MeCN | N Param.: 16.65 sN Param.: 0.58 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Et super-dmap (in MeCN) |
MeCN | N Param.: 16.81 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bn super-dmap (in MeCN) |
MeCN | N Param.: 17.69 sN Param.: 0.57 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Ac super-dmap (in MeCN) |
MeCN | N Param.: 15.39 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bz super-dmap (in MeCN) |
MeCN | N Param.: 14.19 sN Param.: 0.67 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
dipp Imd boronate |
dichloromethane | N Param.: 9.55 sN Param.: 0.81 | | Org. Lett. 2012, 14, 82-85 10.1021/ol202836p |
Me2 Imd boronate |
dichloromethane | N Param.: 11.88 sN Param.: 0.71 | | Org. Lett. 2012, 14, 82-85 10.1021/ol202836p |
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene |
dichloromethane | N Param.: 1.47 sN Param.: 0.89 | | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w |
3,3,3-trifluoro-2-(trimethylsiloxy)propene |
dichloromethane | N Param.: -2.94 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN Param.: 0.46 | | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
hypochlorite (in water) |
water | N Param.: 14.50 sN Param.: 0.58 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
hypobromite (in water) |
water | N Param.: 16.69 sN Param.: 0.46 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
bromite (in water) |
water | N Param.: 12.75 sN Param.: 0.59 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
peroxomonosulfate (in water) |
water | N Param.: 14.41 sN Param.: 0.60 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
glycine (anionic, in water) |
water | N Param.: 13.51 sN Param.: 0.58 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
alanine (anionic, in water) |
water | N Param.: 13.01 sN Param.: 0.58 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
valine (anionic, in water) |
water | N Param.: 13.65 sN Param.: 0.57 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
leucine (anionic, in water) |
water | N Param.: 14.01 sN Param.: 0.52 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
phenylalanine (anionic, in water) |
water | N Param.: 14.12 sN Param.: 0.53 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
proline (anionic, in water) |
water | N Param.: 18.08 sN Param.: 0.50 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
serine (anionic, in water) |
water | N Param.: 13.16 sN Param.: 0.55 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
threonine (anionic, in water) |
water | N Param.: 12.69 sN Param.: 0.60 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
asparagine (anionic, in water) |
water | N Param.: 13.03 sN Param.: 0.53 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glutamine (anionic, in water) |
water | N Param.: 13.45 sN Param.: 0.54 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
arginine (betaine, in water) |
water | N Param.: 12.96 sN Param.: 0.57 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
histidine (anionic, in water) |
water | N Param.: 13.83 sN Param.: 0.54 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
aspartate (dianionic, in water) |
water | N Param.: 13.81 sN Param.: 0.53 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glutamate (dianionic, in water) |
water | N Param.: 13.96 sN Param.: 0.54 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
cysteine (dianionic, in water, S-nucleophile!) |
water | N Param.: 23.43 sN Param.: 0.42 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
methionine (anionic, in water) |
water | N Param.: 13.16 sN Param.: 0.58 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
beta-alanine (anionic, in water) |
water | N Param.: 13.26 sN Param.: 0.58 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
gamma-aminobutyric acid (anionic, in water) |
water | N Param.: 13.55 sN Param.: 0.56 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glycylglycine (anionic, in water) |
water | N Param.: 12.91 sN Param.: 0.59 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glycylglycylglycine (anionic, in water) |
water | N Param.: 12.26 sN 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 sN 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 sN 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 sN Param.: 0.51 | | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
imidazole (in MeCN) |
MeCN | N Param.: 11.47 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
imidazole (in DMSO) |
DMSO | N Param.: 11.58 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
imidazole (in water) |
water | N Param.: 9.63 sN Param.: 0.57 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.90 sN Param.: 0.73 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in water) |
water | N Param.: 9.91 sN Param.: 0.55 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-phenyl-imidazole (in MeCN) |
MeCN | N Param.: 11.31 sN Param.: 0.67 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.74 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in water) |
water | N Param.: 9.45 sN Param.: 0.54 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
4-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.79 sN Param.: 0.77 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2,4-dimethyl-imidazole (in MeCN) |
MeCN | N Param.: 11.51 sN Param.: 0.84 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-(trimethylsilyl)-imidazole (in MeCN) |
MeCN | N Param.: 11.43 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
benzimidazole (in DMSO) |
DMSO | N Param.: 10.50 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-benzimidazole (in MeCN) |
MeCN | N Param.: 10.37 sN Param.: 0.82 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.02 sN Param.: 0.85 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.69 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2,5-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.21 sN Param.: 0.85 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5,6-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 11.08 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methoxy-benzimidazole (in DMSO) |
DMSO | N Param.: 11.00 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
benzotriazole (in MeCN) |
MeCN | N Param.: 7.69 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |