Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)   |
THF | N Param.: 31.92 sN Param.: 0.52 |
 |
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
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[...] |
1,3-Diisopropyl-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 30.25 sN Param.: 0.54 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
cyano((diphenylmethylene)amino)methanide  |
DMSO | N Param.: 29.50 sN Param.: 0.50 |
|
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[...] |
anion of 2-phenyl-propionitrile (in DMSO)  |
DMSO | N Param.: 28.95 sN Param.: 0.58 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
chloro(phenylsulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 28.27 sN Param.: 0.42 |
|
J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
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[...] |
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)  |
DMSO | N Param.: 27.62 sN Param.: 0.53 |
|
Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)  |
DMSO | N Param.: 27.57 sN Param.: 0.53 |
|
Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-PhCH(-)CO2Et (in DMSO)  |
DMSO | N Param.: 27.54 sN Param.: 0.57 |
|
Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)  |
DMSO | N Param.: 27.45 sN Param.: 0.38 |
|
J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)  |
DMSO | N Param.: 27.28 sN Param.: 0.50 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
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[...] |
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 26.90 sN Param.: 0.45 |
|
J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)  |
DMSO | N Param.: 26.71 sN Param.: 0.37 |
|
J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
chloro(phenylsulfonyl)methanide (in DMF)  |
DMF | N Param.: 26.64 sN Param.: 0.64 |
 |
Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329 |
1-mesityl-3-methyl-5-methylene-2,4,6-triphenyl-2,5-dihydropyridin-1-ium-2-ide (in THF)  |
THF | N Param.: 26.16 sN Param.: 0.52 |
|
Angew. Chem. Int. Ed. 2024, , e202318283 10.1002/anie.202318283 |
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)  |
DMSO | N Param.: 25.94 sN Param.: 0.42 |
|
J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
anion of (benzylsulfonyl)benzene (in DMSO)  |
DMSO | N Param.: 25.77 sN Param.: 0.56 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 25.59 sN Param.: 0.51 |
|
J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)  |
MeCN | N Param.: 25.54 sN Param.: 0.35 |
|
Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 |
m-nitrophenolate (in MeCN)  |
MeCN | N Param.: 25.51 sN Param.: 0.43 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
enolate of 3-isochromanone (in DMSO)  |
DMSO | N Param.: 25.39 sN Param.: 0.54 |
|
J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 |
anion of 2-(4-CN-C6H4)propionitrile (in DMSO)  |
DMSO | N Param.: 25.35 sN Param.: 0.56 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 4-cyanobenzyl-CN (in DMSO)  |
DMSO | N Param.: 25.11 sN Param.: 0.54 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 1-phenylpropan-2-one (in DMSO)  |
DMSO | N Param.: 24.99 sN Param.: 0.60 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
4-methoxythiophenolate (in DMSO)  |
DMSO | N Param.: 24.97 sN Param.: 0.68 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 24.88 sN Param.: 0.49 |
|
J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
1,3-bis(2,6-diisopropylphenyl)-5-methyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 24.86 sN Param.: 0.52 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
4-methylthiophenolate (in DMSO)  |
DMSO | N Param.: 24.35 sN Param.: 0.69 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
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 |
potassium indenide (in DMSO)  |
DMSO | N Param.: 24.16 sN Param.: 0.68 |
|
Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
bromo(phenylsulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 23.90 sN Param.: 0.62 |
|
J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
piperidin-1-yl dithiocarbamate (in MeCN)  |
MeCN | N Param.: 23.84 sN Param.: 0.57 |
|
Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j |
sodium indenide (in DMSO)  |
DMSO | N Param.: 23.74 sN Param.: 0.71 |
|
Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
lithium indenide (in DMSO)  |
DMSO | N Param.: 23.66 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)  |
DMSO | N Param.: 23.64 sN Param.: 0.65 |
|
Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
4-methylpiperazin-1-yl dithiocarbamate (in MeCN)  |
MeCN | N Param.: 23.61 sN Param.: 0.57 |
|
Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j |
1,3-Bis(2,6-diisopropylphenyl)-5-(4-methoxyphenyl)-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 23.55 sN Param.: 0.56 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
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 |
cysteine (dianionic, in water)  |
water | N Param.: 23.43 sN Param.: 0.42 |
|
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
m-(trifluoromethyl)phenolate (in DMF)  |
DMF | N Param.: 23.40 sN Param.: 0.51 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
thiophenolate (in DMSO)  |
DMSO | N Param.: 23.36 sN Param.: 0.74 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 23.35 sN Param.: 0.40 |
|
Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)  |
DMSO | N Param.: 23.27 sN Param.: 0.70 |
|
Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
m-(trifluoromethyl)phenolate (in MeCN)  |
MeCN | N Param.: 23.20 sN Param.: 0.51 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
anion of 1,2-diphenylethanone (in DMSO)  |
DMSO | N Param.: 23.15 sN Param.: 0.60 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
trimethylamine (in MeCN)  |
MeCN | N Param.: 23.05 sN Param.: 0.45 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |