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 | |
O-ethyl dithiocarbonate (in MeCN) | MeCN | N Param.: 19.30 sN Param.: 0.69 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
anion of N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO) | DMSO | N Param.: 19.28 sN Param.: 0.65 | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | |
(EtO)2P(O)CH(-)CO2Et (in DMSO) | DMSO | N Param.: 19.23 sN Param.: 0.65 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
anion of diethyl 2-cyclohexylmalonate (in DMSO) | DMSO | N Param.: 19.23 sN Param.: 0.67 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
Ph2P(O)CH(-)CO2Et (in DMSO) | DMSO | N Param.: 19.20 sN Param.: 0.69 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
2-ethoxy-1-methoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) | DMSO | N Param.: 19.15 sN Param.: 0.59 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
benzimidazole anion (in DMSO) | DMSO | N Param.: 19.13 sN Param.: 0.55 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
p-methylphenolate (in DMSO) | DMSO | N Param.: 19.08 sN Param.: 0.87 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) | DMSO | N Param.: 19.03 sN Param.: 0.58 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
p-(trifluoromethyl)phenolate (in DMSO) | DMSO | N Param.: 18.98 sN Param.: 0.63 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
4-pyridone anion (in DMSO) | DMSO | N Param.: 18.97 sN Param.: 0.62 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
4-nitrothiophenolate (in DMSO) | DMSO | N Param.: 18.92 sN Param.: 0.87 | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 | |
N-methyl-piperidine (in CH2Cl2) | dichloromethane | N Param.: 18.90 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
(cyclohexen-1-yl)prolinate (in MeCN) | MeCN | N Param.: 18.86 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 | |
phenolate (in DMF) | DMF | N Param.: 18.86 sN Param.: 0.89 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
anion of ethyl acetylacetate (in DMSO) | DMSO | N Param.: 18.82 sN Param.: 0.69 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) | DMSO | N Param.: 18.81 sN Param.: 0.59 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
m-methoxyphenolate (in MeCN) | MeCN | N Param.: 18.81 sN Param.: 0.80 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
DABCO (in MeCN) | MeCN | N Param.: 18.80 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 | |
3,5-dinitrobenzoate (in acetone) | acetone | N Param.: 18.80 sN Param.: 0.62 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
p-cyanophenolate (in DMSO) | DMSO | N Param.: 18.78 sN Param.: 0.57 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-nitrobenzoate (in acetone) | acetone | N Param.: 18.74 sN Param.: 0.68 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
anion of diethyl 2-(isopropyl)malonate (in DMSO) | DMSO | N Param.: 18.74 sN Param.: 0.71 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
1,3-di-tert-butyl-1,3,2-diazaphospholidine (in MeCN) | MeCN | N Param.: 18.74 sN Param.: 0.47 | Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 | |
N-methyl-piperidine (in MeCN) | MeCN | N Param.: 18.72 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
Ph2P(O)CH(-)CN (in DMSO) | DMSO | N Param.: 18.69 sN Param.: 0.72 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF) | THF | N Param.: 18.68 sN Param.: 0.63 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
anion of benzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Param.: 18.67 sN Param.: 0.68 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO) | DMSO | N Param.: 18.63 sN Param.: 0.82 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
methanesulfonamide anion (in DMSO) | DMSO | N Param.: 18.61 sN Param.: 0.53 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
anion of ethyl cyanoacetate (in 91M9AN) | MeOH-MeCN mix | N Param.: 18.59 sN Param.: 0.65 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
pyrrolidine (inMeCN) | MeCN | N Param.: 18.58 sN Param.: 0.61 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(EtO)2P(O)CH(-)CN (in DMSO) | DMSO | N Param.: 18.57 sN Param.: 0.66 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
peroxybenzoate (in H2O) | water | N Param.: 18.57 sN Param.: 0.43 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
3-chloro-4-methoxyperoxybenzoate (in H2O) | water | N Param.: 18.56 sN Param.: 0.48 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
phenolate (in MeCN) | MeCN | N Param.: 18.53 sN Param.: 0.85 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
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 | |
o-(trifluoromethyl)phenolate (in DMSO) | DMSO | N Param.: 18.47 sN Param.: 0.61 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
magnesium 2-carboperoxybenzoate (in H2O) | water | N Param.: 18.43 sN Param.: 0.46 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
Me2S=CH(p-NO2-C6H4) (in DMSO) | DMSO | N Param.: 18.42 sN Param.: 0.65 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
tris(4-dimethylaminophenyl)phosphane | dichloromethane | N Param.: 18.39 sN Param.: 0.64 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
o-(trifluoromethyl)phenolate (in MeCN) | MeCN | N Param.: 18.39 sN Param.: 0.69 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
anion of 3-methyl acetylacetone (in DMSO) | DMSO | N Param.: 18.38 sN Param.: 0.72 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine | MeCN | N Param.: 18.33 sN Param.: 0.64 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO) | DMSO | N Param.: 18.32 sN Param.: 0.84 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
p-chlorophenolate (in MeCN) | MeCN | N Param.: 18.32 sN Param.: 0.82 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
anion of p-tolylnitromethane (in DMSO) | DMSO | N Param.: 18.31 sN Param.: 0.76 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of phenylnitromethane (in DMSO) | DMSO | N Param.: 18.29 sN Param.: 0.71 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
perhydroazepine (in water) | water | N Param.: 18.29 sN Param.: 0.46 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
O-isopropyl dithiocarbonate (in MeCN) | MeCN | N Param.: 18.27 sN Param.: 0.78 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j |