Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
10% methanol/90% MeCN (v/v) | MeOH-MeCN mix | N Param.: 5.55 sN Param.: 0.97 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
thiocyanate (in MeCN) | MeCN | N Param.: 17.94 sN Param.: 0.60 | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u | |
thiocyanate (in MeCN) | MeCN | N Param.: 12.13 sN Param.: 0.60 | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u | |
chloride (in MeOH) | MeOH | N Param.: 12.90 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50/50 MeOH/MeCN) | MeOH-MeCN mix | N Param.: 14.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in EtOH) | EtOH | N Param.: 14.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 80% aq EtOH) | water-EtOH mix | N Param.: 13.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50% aq EtOH) | water-EtOH mix | N Param.: 11.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in H2O) | water | N Param.: 10.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 20% aq MeCN) | water-MeCN mix | N Param.: 11.31 sN Param.: 0.58 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 40% aq MeCN) | water-MeCN mix | N Param.: 11.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50% aq MeCN) | water-MeCN mix | N Param.: 12.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 60% aq MeCN) | water-MeCN mix | N Param.: 12.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 80% aq MeCN) | water-MeCN mix | N Param.: 13.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in MeCN) | MeCN | N Param.: 17.20 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in CF3CH2OH) | TFE | N Param.: 10.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in hexafluoroisopropanol) | HFIP | N Param.: 8.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
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 | |
bromide (in 50% aq EtOH) | water-EtOH mix | N Param.: 13.60 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in H2O) | water | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 20% aq MeCN) | water-MeCN mix | N Param.: 12.20 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 40% aq MeCN) | water-MeCN mix | N Param.: 12.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 50% aq MeCN) | water-MeCN mix | N Param.: 13.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in CF3CH2OH) | TFE | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
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 | |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Param.: 16.28 sN Param.: 0.75 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Param.: 17.33 sN Param.: 0.74 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
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 | |
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 | |
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.66 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
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 | |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Param.: 20.72 sN Param.: 0.58 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
Ph3P=CH-CO2Et | dichloromethane | N Param.: 12.79 sN Param.: 0.77 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
Ph3P=CH-CO2Et (in DMSO) | DMSO | N Param.: 12.21 sN Param.: 0.62 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
Ph3P=C(CH3)-CO2Et | dichloromethane | N Param.: 13.09 sN Param.: 0.73 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
Ph3P=CH-CN | dichloromethane | N Param.: 12.29 sN Param.: 0.75 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
Ph3P=CH-COPh | dichloromethane | N Param.: 9.54 sN Param.: 0.97 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
(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 | |
(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 | |
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 | |
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 | |
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 | |
benzylamine (in DMSO) | DMSO | N Param.: 15.28 sN Param.: 0.65 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
1-aminopropan-2-ol (in DMSO) | DMSO | N Param.: 15.47 sN Param.: 0.65 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
diethanolamine (in DMSO) | DMSO | N Param.: 15.51 sN Param.: 0.70 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
ethanolamine (in DMSO) | DMSO | N Param.: 16.07 sN Param.: 0.61 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
phenylsulfinate (in DMSO) | DMSO | N Param.: 19.60 sN Param.: 0.60 | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | |
phenylsulfinate (in MeCN) | MeCN | N Param.: 20.11 sN Param.: 0.59 | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | |
phenylsulfinate (in 50W50AN) | water-MeCN mix | N Param.: 13.75 sN Param.: 0.68 | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | |
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 | |
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 | |
2-pyridone anion (in water) | water | N Param.: 12.47 sN Param.: 0.52 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
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-pyridone anion (in MeCN) | MeCN | N Param.: 20.22 sN Param.: 0.49 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
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 | |
DMSO (O attack) | DMSO | N Param.: 11.30 sN Param.: 0.74 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO) | DMSO | N Param.: 13.78 sN Param.: 0.72 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
(C6H5)-(CO)-CH=SMe2 (in DMSO) | DMSO | N Param.: 13.95 sN Param.: 0.69 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
(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 | |
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO) | DMSO | N Param.: 15.68 sN Param.: 0.65 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
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 | |
Me2S=CH(4-CN-C6H4) (in DMSO) | DMSO | N Param.: 21.07 sN Param.: 0.68 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
Me2S(O)=CH2 (in DMSO) | DMSO | N Param.: 21.29 sN Param.: 0.47 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
acetate (in MeCN) | MeCN | N Param.: 16.90 sN Param.: 0.75 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
acetate (in 90A10W) | aq acetone | N Param.: 12.71 sN Param.: 0.68 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
acetate (in 80A20W) | aq acetone | N Param.: 12.50 sN Param.: 0.60 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
benzoate (in MeCN) | MeCN | N Param.: 16.82 sN Param.: 0.70 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
benzoate (in 90AN10W) | aq MeCN | N Param.: 11.30 sN Param.: 0.72 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
p-nitrobenzoate (in MeCN) | MeCN | N Param.: 15.30 sN Param.: 0.76 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
p-nitrobenzoate (in acetone) | acetone | N Param.: 18.74 sN Param.: 0.68 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
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 | |
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 | |
2-methyl-pent-1-ene | dichloromethane | N Param.: 0.84 sN Param.: 1.06 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
1-(N-piperidino)cyclohexene (in MeCN) | MeCN | N Param.: 14.02 sN Param.: 0.76 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN) | MeCN | N Param.: 12.34 sN Param.: 0.72 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN) | MeCN | N Param.: 10.52 sN Param.: 0.78 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN) | MeCN | N Param.: 9.11 sN Param.: 0.88 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
n-butyl vinyl ether | dichloromethane | N Param.: 3.76 sN Param.: 0.91 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
acetonitrile (in MeCN) | MeCN | N Param.: 2.23 sN Param.: 0.84 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
potassium trifluoro(1-methyl-1H-indol-2-yl)borate | MeCN | N Param.: 9.55 sN Param.: 1.16 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
potassium trifluoro(1-methyl-1H-indol-5-yl)borate | MeCN | N Param.: 8.77 sN Param.: 1.09 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate | MeCN | N Param.: 6.46 sN Param.: 0.96 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate | MeCN | N Param.: 7.10 sN Param.: 1.18 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate | MeCN | N Param.: 4.06 sN Param.: 0.79 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
tert-butyl indole-1-carboxylate | MeCN | N Param.: 1.68 sN Param.: 1.26 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
potassium trifluoro(furan-2-yl)borate | MeCN | N Param.: 5.99 sN Param.: 0.79 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
potassium trifluoro(furan-3-yl)borate | MeCN | N Param.: 6.83 sN Param.: 0.93 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
potassium trifluoro(3-methoxy-thiophen-2-yl)borate | MeCN | N Param.: 7.32 sN Param.: 0.90 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
3-methoxythiophene | MeCN | N Param.: 3.06 sN Param.: 1.19 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO) | DMSO | N Param.: 26.71 sN Param.: 0.37 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO) | DMSO | N Param.: 27.45 sN Param.: 0.38 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
cyano(pyridin-1-ium-1-yl)methanide (in DMSO) | DMSO | N Param.: 25.94 sN Param.: 0.42 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
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 | |
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-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO) | DMSO | N Param.: 21.61 sN Param.: 0.58 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO) | DMSO | N Param.: 17.98 sN Param.: 0.63 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
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 | |
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 | |
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2) | dichloromethane | N Param.: 1.88 sN Param.: 0.96 | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y | |
1,3,5-trimethylcyclohexa-1,4-diene (in CH2Cl2) | dichloromethane | N Param.: 4.95 sN Param.: 0.79 | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y |