Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 11.20 sN Param.: 0.64 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 9.49 sN Param.: 0.82 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
(E)-1-(2-(4-methoxyphenyl)-1-phenylvinyl)pyrrolidine (in MeCN) | MeCN | N Param.: 11.99 sN Param.: 0.84 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-1-(1,2-diphenylvinyl)pyrrolidine (in MeCN) | MeCN | N Param.: 11.66 sN Param.: 0.82 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN) | MeCN | N Param.: 10.63 sN Param.: 0.84 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN) | MeCN | N Param.: 10.42 sN Param.: 0.82 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN) | MeCN | N Param.: 9.94 sN Param.: 0.86 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN) | MeCN | N Param.: 8.78 sN Param.: 0.83 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-beta-(N-piperidino)styrene (in MeCN) | MeCN | N Param.: 13.84 sN Param.: 0.73 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-4-styrylmorpholine | MeCN | N Param.: 11.66 sN Param.: 0.83 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
alpha-(N-piperidino)styrene (in MeCN) | MeCN | N Param.: 11.60 sN Param.: 0.80 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
alpha-(N-morpholino)styrene (in MeCN) | MeCN | N Param.: 10.30 sN Param.: 0.80 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
hypochlorite (in water) | water | N Param.: 14.50 sN Param.: 0.58 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
hypobromite (in water) | water | N Param.: 16.69 sN Param.: 0.46 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
bromite (in water) | water | N Param.: 12.75 sN Param.: 0.59 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
peroxomonosulfate (in water) | water | N Param.: 14.41 sN Param.: 0.60 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
(p-nitrophenyl)diazomethane | dichloromethane | N Param.: 7.17 sN Param.: 0.83 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
(p-cyanophenyl)diazomethane | dichloromethane | N Param.: 7.66 sN Param.: 0.80 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
(p-bromophenyl)diazomethane | dichloromethane | N Param.: 8.87 sN Param.: 0.82 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
beta-piperidinium-peroxypropionate | water | N Param.: 13.94 sN Param.: 0.62 | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 | |
peroxy-beta-alanate | water | N Param.: 14.07 sN Param.: 0.56 | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 | |
peroxy-GABA | water | N Param.: 14.33 sN Param.: 0.57 | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 | |
1-(trimethylsiloxy)cyclopentene (in MeCN) | MeCN | N Param.: 6.43 sN Param.: 0.89 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
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[...] | |
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[...] | |
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[...] | |
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[...] | |
cyano((diphenylmethylene)amino)methanide | DMSO | N Param.: 29.50 sN Param.: 0.50 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN) | MeCN | N Param.: 3.00 sN Param.: 0.83 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN) | MeCN | N Param.: 5.18 sN Param.: 0.94 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
3-(trimethylsiloxy)-1H-indene (in MeCN) | MeCN | N Param.: 7.32 sN Param.: 0.82 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN) | MeCN | N Param.: 5.06 sN Param.: 0.91 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
3-pyrrolidino-1H-indene (in MeCN) | MeCN | N Param.: 15.27 sN Param.: 0.93 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN) | MeCN | N Param.: 14.09 sN Param.: 0.66 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO) | DMSO | N Param.: 16.26 sN Param.: 0.83 | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 | |
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 | |
1,3-di-tert-butyl-2,3-dihydro-1H-benzo[d][1,3,2]diazaphosphole (in MeCN) | MeCN | N Param.: 20.93 sN Param.: 0.43 | Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 | |
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-di-tert-butyl-1,3,2-diazaphosphinane (in MeCN) | MeCN | N Param.: 13.46 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 | |
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 | |
1,3-dimesityl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN) | MeCN | N Param.: 17.68 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 | |
Ph3P=CH-CHO (in MeCN) | MeCN | N Param.: 9.09 sN Param.: 0.74 | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 | |
Ph3P=CH-C(O)Me (in MeCN) | MeCN | N Param.: 10.27 sN Param.: 0.83 | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 | |
cysteine (dianionic, in water) | water | N Param.: 23.43 sN Param.: 0.42 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
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 | |
p-nitrophenolate (in MeCN) | MeCN | N Param.: 15.14 sN Param.: 0.82 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-nitrophenolate (in DMF) | DMF | N Param.: 15.05 sN Param.: 0.80 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
o-nitrophenolate (in DMSO) | DMSO | N Param.: 15.48 sN Param.: 0.71 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
o-nitrophenolate (in MeCN) | MeCN | N Param.: 15.83 sN Param.: 0.80 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
o-nitrophenolate (in DMF) | DMF | N Param.: 16.65 sN Param.: 0.70 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
m-nitrophenolate (in DMSO) | DMSO | N Param.: 21.29 sN Param.: 0.54 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
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 | |
m-nitrophenolate (in DMF) | DMF | N Param.: 22.41 sN Param.: 0.54 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
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-cyanophenolate (in MeCN) | MeCN | N Param.: 19.58 sN Param.: 0.59 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-cyanophenolate (in DMF) | DMF | N Param.: 17.85 sN Param.: 0.71 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
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 | |
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 | |
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-(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 | |
p-(trifluoromethyl)phenolate (in MeCN) | MeCN | N Param.: 21.69 sN Param.: 0.53 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-(trifluoromethyl)phenolate (in DMF) | DMF | N Param.: 22.05 sN Param.: 0.53 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
m-(trifluoromethyl)phenolate (in DMSO) | DMSO | N Param.: 22.62 sN Param.: 0.51 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
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 | |
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 | |
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 | |
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 | |
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 | |
phenolate (in DMSO) | DMSO | N Param.: 19.86 sN Param.: 0.71 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
phenolate (in MeCN) | MeCN | N Param.: 18.53 sN Param.: 0.85 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
phenolate (in DMF) | DMF | N Param.: 18.86 sN Param.: 0.89 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
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 | |
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 | |
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-(tert-butyl)phenolate (in MeCN) | MeCN | N Param.: 21.70 sN Param.: 0.58 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
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 DMSO) | DMSO | N Param.: 20.09 sN Param.: 0.80 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-methoxyphenolate (in MeCN) | MeCN | N Param.: 20.62 sN Param.: 0.69 | 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 | |
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 | |
o,o'-di-tert-butylphenolate (in DMSO) | DMSO | N Param.: 21.02 sN Param.: 0.59 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-methylphenolate (in H2O) | water | N Param.: 14.30 sN Param.: 0.55 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
glutathione GSH(NH3+/S-) | water | N Param.: 20.97 sN Param.: 0.56 | Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803 | |
prolinate (in MeCN) | MeCN | N Param.: 19.95 sN Param.: 0.68 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
2-methylpyrrolidine (in MeCN) | MeCN | N Param.: 16.78 sN Param.: 0.71 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
pyrrolidine (inMeCN) | MeCN | N Param.: 18.58 sN Param.: 0.61 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(R)-2-isopropylpyrrolidine | MeCN | N Param.: 16.44 sN Param.: 0.71 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
2,2-dimethylpyrrolidine | MeCN | N Param.: 13.96 sN Param.: 0.76 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
2-benzylpyrrolidine | MeCN | N Param.: 17.43 sN Param.: 0.66 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(S)-2-benzhydrylpyrrolidine | MeCN | N Param.: 16.61 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(S)-pyrrolidin-2-ylmethanamine | MeCN | N Param.: 17.24 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine | MeCN | N Param.: 17.41 sN Param.: 0.68 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(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 | |
(S)-2-(azidomethyl)pyrrolidine | MeCN | N Param.: 15.43 sN Param.: 0.73 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(S)-pyrrolidin-2-ylmethanol | MeCN | N Param.: 16.74 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(S)-2-(methoxymethyl)pyrrolidine | MeCN | N Param.: 16.50 sN Param.: 0.71 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
2-(trifluoromethyl)pyrrolidine | MeCN | N Param.: 11.34 sN Param.: 0.73 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
methyl L-prolinate | MeCN | N Param.: 14.75 sN Param.: 0.82 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
(S)-N,N-dimethylpyrrolidine-2-carboxamide | MeCN | N Param.: 17.61 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |