C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
(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 |
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 |
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 |
(E)-1-styrylpyrrolidine (in CH2Cl2) |
dichloromethane | N Param.: 12.26 sN Param.: 0.93 | | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2) |
dichloromethane | N Param.: 10.19 sN Param.: 1.06 | | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
(E)-1-styryl-2-(triphenylsilyl)pyrrolidine (in CH2Cl2) |
dichloromethane | N Param.: 11.77 sN Param.: 0.98 | | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
Meldrum's acid iodonium ylide (in CH2Cl2) |
dichloromethane | N Param.: 4.36 sN Param.: 1.06 | | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
Dimedone iodonium ylide (in CH2Cl2) |
dichloromethane | N Param.: 6.18 sN Param.: 0.81 | | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2) |
dichloromethane | N Param.: 7.98 sN Param.: 0.71 | | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2) |
dichloromethane | N Param.: 4.67 sN Param.: 0.92 | | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
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 |
(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 |
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 |
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 |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN) |
MeCN | N Param.: 16.15 sN Param.: 0.99 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN) |
MeCN | N Param.: 15.62 sN Param.: 0.99 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-nitrobenzyl-CN (in MeCN) |
MeCN | N Param.: 20.10 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN) |
MeCN | N Param.: 19.90 sN Param.: 0.66 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 11.00 sN Param.: 0.57 | | J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493 |
Indole |
dichloromethane | N Param.: 5.55 sN Param.: 1.09 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
N-methylindole |
dichloromethane | N Param.: 5.75 sN Param.: 1.23 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
1,2-dimethylindole |
dichloromethane | N Param.: 6.54 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2-(bis(trimethylsiloxy)amino)propene |
dichloromethane | N Param.: 4.76 sN Param.: 0.86 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
(bis(trimethylsiloxy)amino)styrene |
dichloromethane | N Param.: 4.80 sN Param.: 0.86 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
2-(bis(tert-butyldimethylsiloxy)amino)propene |
dichloromethane | N Param.: 4.23 sN Param.: 0.93 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester |
dichloromethane | N Param.: 3.84 sN Param.: 0.87 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
anion of nitroethane (in DMSO) |
DMSO | N Param.: 21.54 sN Param.: 0.62 | | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 |
anion of nitroethane (in water) |
water | N Param.: 11.25 sN Param.: 0.52 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of nitromethane (in water) |
water | N Param.: 12.06 sN Param.: 0.53 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of nitromethane (in DMSO) |
DMSO | N Param.: 20.71 sN Param.: 0.60 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-nitropropane (in DMSO) |
DMSO | N Param.: 20.61 sN Param.: 0.69 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-nitropropane (in water) |
water | N Param.: 10.69 sN Param.: 0.56 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of phenylnitromethane (in H2O) |
water | N Param.: 12.05 sN Param.: 0.53 | | 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 |
anion of p-tolylnitromethane (in water) |
water | N Param.: 13.09 sN Param.: 0.50 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
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 (4-nitrophenyl)nitromethane (in water) |
water | N Param.: 13.58 sN Param.: 0.52 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-nitrophenyl)nitromethane (in DMSO) |
DMSO | N Param.: 16.29 sN Param.: 0.75 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (3-nitrophenyl)nitromethane (in water) |
water | N Param.: 14.25 sN Param.: 0.46 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (3-nitrophenyl)nitromethane (in DMSO) |
DMSO | N Param.: 18.06 sN Param.: 0.71 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-cyanophenyl)nitromethane (in water) |
water | N Param.: 13.23 sN Param.: 0.52 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-cyanophenyl)nitromethane (in DMSO) |
DMSO | N Param.: 16.96 sN Param.: 0.73 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
5-methoxy-indole |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-amino-indole |
MeCN | N Param.: 7.22 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-hydroxy-indole |
MeCN | N Param.: 6.44 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methyl-indole |
MeCN | N Param.: 6.00 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-indole |
MeCN | N Param.: 4.42 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-bromo-indole |
MeCN | N Param.: 4.38 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-cyano-indole |
MeCN | N Param.: 2.83 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
1H-indole-5-carboxylic acid |
MeCN | N Param.: 3.97 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methoxy-2-methylindole |
MeCN | N Param.: 7.26 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2,5-dimethylindole |
MeCN | N Param.: 7.22 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2-methylindole |
MeCN | N Param.: 6.91 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |