Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
Bu4NBH4 (in DMSO) | DMSO | N Param.: 14.94 sN Param.: 0.79 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO) | DMSO | N Param.: 14.94 sN Param.: 0.96 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
1-(N-pyrrolidino)cyclohexene | dichloromethane | N Param.: 14.91 sN Param.: 0.86 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
4-(dimethylamino)pyridine (in DMF) | DMF | N Param.: 14.90 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
3,5-dinitrobenzoate (in MeCN) | MeCN | N Param.: 14.90 sN Param.: 0.71 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
1,3-diethyl-thiobarbiturate anion (in DMSO) | DMSO | N Param.: 14.90 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
tris(2,4-dimethylphenyl)phosphane | dichloromethane | N Param.: 14.88 sN Param.: 0.41 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
maleimide anion (in DMSO) | DMSO | N Param.: 14.87 sN Param.: 0.76 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
4-nitro-imidazole anion (in DMSO) | DMSO | N Param.: 14.81 sN Param.: 0.71 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
4-(dimethylamino)pyridine (in DMSO) | DMSO | N Param.: 14.80 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-(morpholino)pyridine (in MeCN) | MeCN | N Param.: 14.80 sN Param.: 0.63 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
theophylline anion (in DMSO) | DMSO | N Param.: 14.78 sN Param.: 0.71 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
MeO-Breslow 1a | THF | N Param.: 14.77 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
4-pyridone anion (in water) | water | N Param.: 14.76 sN Param.: 0.48 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
anion of (3-nitrophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.75 sN Param.: 0.71 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
methyl L-prolinate | MeCN | N Param.: 14.75 sN Param.: 0.82 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
NaBH4 (in DMSO) | DMSO | N Param.: 14.74 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
chloride (in EtOH) | EtOH | N Param.: 14.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
diethylamine (in water) | water | N Param.: 14.68 sN Param.: 0.53 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
tricyclohexylphosphane | dichloromethane | N Param.: 14.64 sN Param.: 0.68 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2) | dichloromethane | N Param.: 14.62 sN Param.: 0.72 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
4-(morpholino)pyridine (in CH2Cl2) | dichloromethane | N Param.: 14.59 sN Param.: 0.69 | Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572 | |
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO) | DMSO | N Param.: 14.58 sN Param.: 0.79 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine | dichloromethane | N Param.: 14.57 sN Param.: 0.75 | Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730 | |
azide ion (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.54 sN Param.: 0.82 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
methanolate (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.51 sN Param.: 0.68 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
dipropylamine (in MeCN) | MeCN | N Param.: 14.51 sN Param.: 0.80 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
bromide (in 80% aq EtOH) | water-EtOH mix | N Param.: 14.50 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
hypochlorite (in water) | water | N Param.: 14.50 sN Param.: 0.58 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Param.: 14.49 sN Param.: 0.86 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO) | DMSO | N Param.: 14.48 sN Param.: 0.71 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 14.48 sN Param.: 0.86 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO) | DMSO | N Param.: 14.46 sN Param.: 0.91 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
NaB(OAc)3H (in DMSO) | DMSO | N Param.: 14.45 sN Param.: 0.76 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine) | dichloromethane | N Param.: 14.45 sN Param.: 0.78 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
Desoxy Breslow intermediate 2a' | THF | N Param.: 14.45 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO) | dichloromethane | N Param.: 14.44 sN Param.: 0.79 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD) | dichloromethane | N Param.: 14.43 sN Param.: 0.81 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN) | MeCN | N Param.: 14.43 sN Param.: 0.79 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
peroxomonosulfate (in water) | water | N Param.: 14.41 sN Param.: 0.60 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in DMSO) | DMSO | N Param.: 14.40 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF) | THF | N Param.: 14.40 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
2-aminobutan-1-ol (in DMSO) | DMSO | N Param.: 14.39 sN Param.: 0.67 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
allylamine (in MeCN) | MeCN | N Param.: 14.37 sN Param.: 0.66 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
2-benzyl-1,1,3,3-tetramethylguanidine | dichloromethane | N Param.: 14.36 sN Param.: 0.79 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
triphenylphosphane | dichloromethane | N Param.: 14.33 sN Param.: 0.65 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
anion of 3-methyl acetylacetone (in water) | water | N Param.: 14.33 sN Param.: 0.69 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
peroxy-GABA | water | N Param.: 14.33 sN Param.: 0.57 | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 | |
p-nitrophenolate (in DMSO) | DMSO | N Param.: 14.32 sN Param.: 0.77 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
ethyl glycinate (in DMSO) | DMSO | N Param.: 14.30 sN Param.: 0.67 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |