Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
N-methyl-pyrrolidine (in MeCN) | MeCN | N Param.: 20.59 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
quinuclidine (in MeCN) | MeCN | N Param.: 20.54 sN Param.: 0.60 | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 | |
2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) | DMSO | N Param.: 20.51 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
azide ion (in DMSO) | DMSO | N Param.: 20.50 sN Param.: 0.59 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
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.[...] | |
o-(trifluoromethyl)phenolate (in DMF) | DMF | N Param.: 20.37 sN Param.: 0.58 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-chlorophenolate (in DMSO) | DMSO | N Param.: 20.34 sN Param.: 0.64 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
cyanamide anion (in DMSO) | DMSO | N Param.: 20.33 sN Param.: 0.64 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO) | DMSO | N Param.: 20.24 sN Param.: 0.60 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
anion of diethyl malonate (in DMSO) | DMSO | N Param.: 20.22 sN Param.: 0.65 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
4-pyridone anion (in MeCN) | MeCN | N Param.: 20.22 sN Param.: 0.49 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
phenylsulfinate (in MeCN) | MeCN | N Param.: 20.11 sN Param.: 0.59 | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | |
2-pyridone anion (in MeCN) | MeCN | N Param.: 20.11 sN Param.: 0.57 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
anion of 4-nitrobenzyl-CN (in MeCN) | MeCN | N Param.: 20.10 sN Param.: 0.71 | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 | |
p-methoxyphenolate (in DMSO) | DMSO | N Param.: 20.09 sN Param.: 0.80 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO) | DMSO | N Param.: 20.08 sN Param.: 0.57 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
1,2,3-trimethoxy-1,3-dioxopropan-2-ide (in DMSO) | DMSO | N Param.: 20.08 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO) | DMSO | N Param.: 20.02 sN Param.: 0.76 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO) | DMSO | N Param.: 20.00 sN Param.: 0.71 | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 | |
prolinate (in MeCN) | MeCN | N Param.: 19.95 sN Param.: 0.68 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
bis(4-nitrophenyl)methanide (in DMSO) | DMSO | N Param.: 19.92 sN Param.: 0.67 | ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...] | |
2-pyridone anion (in DMSO) | DMSO | N Param.: 19.91 sN Param.: 0.60 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO) | DMSO | N Param.: 19.91 sN Param.: 0.62 | Eur. J. Org. Chem. 2024, , accepted 10.1002/ejoc.202400373 | |
p-(tert-butyl)phenolate (in DMF) | DMF | N Param.: 19.90 sN Param.: 0.80 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-methoxyphenolate (in DMF) | DMF | N Param.: 19.90 sN Param.: 0.82 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN) | MeCN | N Param.: 19.90 sN Param.: 0.66 | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 | |
phenolate (in DMSO) | DMSO | N Param.: 19.86 sN Param.: 0.71 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN) | MeCN | N Param.: 19.85 sN Param.: 0.34 | Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 | |
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole | THF | N Param.: 19.84 sN Param.: 0.58 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
3,5-bis(trifluoromethyl)thiophenolate (in DMSO) | DMSO | N Param.: 19.71 sN Param.: 0.86 | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 | |
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in MeCN) | MeCN | N Param.: 19.69 sN Param.: 0.61 | Eur. J. Org. Chem. 2024, , accepted 10.1002/ejoc.202400373 | |
anion of 4-nitrobenzyl-CN (in DMSO) | DMSO | N Param.: 19.67 sN Param.: 0.68 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
p-chlorophenolate (in DMF) | DMF | N Param.: 19.67 sN Param.: 0.72 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-(tert-butyl)phenolate (in DMSO) | DMSO | N Param.: 19.67 sN Param.: 0.79 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-methylphenolate (in DMF) | DMF | N Param.: 19.65 sN Param.: 0.85 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
anion of ethyl cyanoacetate (in DMSO) | DMSO | N Param.: 19.62 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO) | DMSO | N Param.: 19.61 sN Param.: 0.60 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
phenylsulfinate (in DMSO) | DMSO | N Param.: 19.60 sN Param.: 0.60 | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | |
1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO) | DMSO | N Param.: 19.58 sN Param.: 0.73 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
p-cyanophenolate (in MeCN) | MeCN | N Param.: 19.58 sN Param.: 0.59 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide | DMSO | N Param.: 19.53 sN Param.: 0.83 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
anion of malononitrile (in water) | water | N Param.: 19.50 sN Param.: 0.55 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Param.: 19.49 sN Param.: 0.63 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO) | DMSO | N Param.: 19.46 sN Param.: 0.58 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
1-methyl-2-methylene-3-phenyl-1,2-dihydropyridine (in DMSO) | DMSO | N Param.: 19.41 sN Param.: 0.61 | Eur. J. Org. Chem. 2024, , accepted 10.1002/ejoc.202400373 | |
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO) | DMSO | N Param.: 19.38 sN Param.: 0.50 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
anion of malononitrile (in DMSO) | DMSO | N Param.: 19.36 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
1-(4-(tert-butyl)phenyl)-2-methylene-4,6-diphenyl-1,2-dihydropyridine (in DMSO) | DMSO | N Param.: 19.36 sN Param.: 0.68 | Eur. J. Org. Chem. 2024, , accepted 10.1002/ejoc.202400373 | |
anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Param.: 19.35 sN Param.: 0.67 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2) | dichloromethane | N Param.: 19.31 sN Param.: 0.46 | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 |