Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 | |
(E)-1-styrylpyrrolidine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.87 sN Param.: 0.76 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(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-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 | |
methanol (in MeCN)![]() ![]() |
MeCN | N Param.: 6.86 sN Param.: 0.73 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
ethanol (in MeCN)![]() ![]() |
MeCN | N Param.: 7.13 sN Param.: 0.71 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
isopropanol (in MeCN)![]() ![]() |
MeCN | N Param.: 6.82 sN Param.: 0.70 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
tert-butanol (in MeCN)![]() ![]() |
MeCN | N Param.: 5.35 sN Param.: 0.72 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
water (in MeCN)![]() ![]() |
MeCN | N Param.: 5.79 sN Param.: 0.72 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
chloro(phenylsulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 28.27 sN Param.: 0.42 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
bromo(phenylsulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 23.90 sN Param.: 0.62 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 25.59 sN Param.: 0.51 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 24.88 sN Param.: 0.49 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 26.90 sN Param.: 0.45 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)![]() ![]() |
DMSO | N Param.: 15.85 sN Param.: 1.04 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
anion of 2-phenylmalononitrile (in DMSO)![]() ![]() |
DMSO | N Param.: 15.58 sN Param.: 1.00 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)![]() ![]() |
DMSO | N Param.: 15.97 sN Param.: 0.72 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)![]() ![]() |
DMSO | N Param.: 15.07 sN Param.: 0.79 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)![]() ![]() |
DMSO | N Param.: 14.99 sN Param.: 0.83 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
ditert-butyl-phenylphosphane![]() ![]() |
dichloromethane | N Param.: 12.40 sN Param.: 0.55 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris(2,6-dimethoxyphenyl)phosphane![]() ![]() |
dichloromethane | N Param.: 15.19 sN Param.: 0.88 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
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 | |
tris(2,6-dimethoxyphenyl)phosphane (in MeCN)![]() ![]() |
MeCN | N Param.: 18.11 sN Param.: 0.62 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris(2-methoxyphenyl)phosphane![]() ![]() |
dichloromethane | N Param.: 14.26 sN Param.: 0.73 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris(2-methylphenyl)phosphane![]() ![]() |
dichloromethane | N Param.: 8.56 sN Param.: 0.70 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
t-butylperoxy anion (in H2O)![]() ![]() |
water | N Param.: 14.29 sN Param.: 0.51 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
cumene peroxy anion (in H2O)![]() ![]() |
water | N Param.: 13.92 sN Param.: 0.61 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
phthalimidoperoxyhexanoate (in H2O)![]() ![]() |
water | N Param.: 16.02 sN Param.: 0.54 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
2-phenylperoxyacetate (in H2O)![]() ![]() |
water | N Param.: 15.63 sN Param.: 0.56 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
3,5-dichloroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.93 sN Param.: 0.50 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
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 | |
3-chloroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 18.19 sN Param.: 0.47 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
4-fluoroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.99 sN Param.: 0.47 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
4-nitroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.43 sN Param.: 0.50 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
4-methoxyperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.84 sN Param.: 0.46 | 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 | |
peroxybenzoate (in H2O)![]() ![]() |
water | N Param.: 18.57 sN Param.: 0.43 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
barbiturate anion (in DMSO)![]() ![]() |
DMSO | N Param.: 15.59 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
1,3-dimethylbarbiturate anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.46 sN Param.: 0.72 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
2-thiobarbiturate anion (in DMSO)![]() ![]() |
DMSO | N Param.: 14.24 sN Param.: 0.82 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
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 | |
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: -0.64 sN Param.: 1.10 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
potassium allyltrifluoroborate (in MeCN)![]() ![]() |
MeCN | N Param.: 5.29 sN Param.: 0.87 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 8.71 sN Param.: 0.80 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
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 | |
pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.60 sN Param.: 0.60 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2-methylpyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 10.52 sN Param.: 0.78 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2-methylpyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 10.98 sN Param.: 0.66 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2,6-dimethylpyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 9.87 sN Param.: 0.68 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2,6-dimethylpyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 9.11 sN Param.: 0.69 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2,4,6-trimethylpyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 9.34 sN Param.: 0.71 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2,4,6-trimethylpyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 9.39 sN Param.: 0.60 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
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 | |
anion of diethyl 2-butylmalonate (in DMSO)![]() ![]() |
DMSO | N Param.: 23.00 sN Param.: 0.55 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
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 | |
anion of diethyl 2-phenylmalonate (in DMSO)![]() ![]() |
DMSO | N Param.: 15.93 sN Param.: 0.99 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
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 | |
anion of triethyl methanetricarboxylate (in DMSO)![]() ![]() |
DMSO | N Param.: 15.33 sN Param.: 0.72 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
anion of diethyl 2-(acetyl)malonate (in DMSO)![]() ![]() |
DMSO | N Param.: 13.83 sN Param.: 0.84 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
anion of diethyl 2-(benzoyl)malonate (in DMSO)![]() ![]() |
DMSO | N Param.: 13.63 sN Param.: 0.80 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
anion of 5-phenyl Meldrum's acid (in DMSO)![]() ![]() |
DMSO | N Param.: 11.54 sN Param.: 0.95 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
anion of 5-(p-anisyl) Meldrum's acid (in DMSO)![]() ![]() |
DMSO | N Param.: 12.35 sN Param.: 0.90 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
anion of diethyl 2-(p-anisyl)malonate (in DMSO)![]() ![]() |
DMSO | N Param.: 16.73 sN Param.: 0.91 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
nicotine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 10.40 sN Param.: 1.04 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 | |
nicotine (in MeCN)![]() ![]() |
MeCN | N Param.: 11.60 sN Param.: 0.81 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 | |
3-methylpyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 10.90 sN Param.: 0.93 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |





































































































