Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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 |