C-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(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 |
anion of Meldrums acid (in DMSO)  |
DMSO | N Param.: 13.91 sN Param.: 0.86 |
|
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
Desoxy Breslow intermediate 2b  |
THF | N Param.: 13.91 sN Param.: 0.64 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
anion of 2-nitro-1-phenylethan-1-one (in DMSO)  |
DMSO | N Param.: 13.91 sN Param.: 0.76 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of (4-cyanophenyl)nitromethane (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 13.92 sN Param.: 0.74 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
(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 |
anion of nitromethane (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 14.02 sN Param.: 0.61 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
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 |
anion of (4-nitrophenyl)nitromethane (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 14.05 sN Param.: 0.72 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)  |
THF | N Param.: 14.07 sN Param.: 0.84 |
|
Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
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 |
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 |
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-methyl acetylacetone (in water)  |
water | N Param.: 14.33 sN Param.: 0.69 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
(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 |
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 |
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 |
(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 |
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 (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 |
MeO-Breslow 1a  |
THF | N Param.: 14.77 sN Param.: 0.80 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
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 |
1-(N-pyrrolidino)cyclohexene  |
dichloromethane | N Param.: 14.91 sN Param.: 0.86 |
|
Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
methyl (cyclohexen-1-yl)prolinate (in MeCN)  |
MeCN | N Param.: 14.96 sN Param.: 0.68 |
|
Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
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 |
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)  |
DMSO | N Param.: 15.02 sN Param.: 0.75 |
|
Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
1-(N-piperidino)cyclopentene  |
dichloromethane | N Param.: 15.06 sN Param.: 0.82 |
|
Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)  |
DMSO | N Param.: 15.13 sN Param.: 0.75 |
|
Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
anion of ethyl 2-nitroacetate (in DMSO)  |
DMSO | N Param.: 15.24 sN Param.: 0.74 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
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 |
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)  |
THF | N Param.: 15.33 sN Param.: 0.79 |
|
Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 |
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 ethyl cyanoacetate (in water)  |
water | N Param.: 15.57 sN Param.: 0.58 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
Dexoxy Breslow intermediate 6  |
THF | N Param.: 15.58 sN Param.: 0.57 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
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 |
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 |
(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO)  |
DMSO | N Param.: 15.60 sN Param.: 0.51 |
|
Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
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 |
MeO-Breslow 1e  |
THF | N Param.: 15.65 sN Param.: 0.52 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
(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 |
bis(phenylsulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 15.68 sN Param.: 0.74 |
|
Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
Me2S=CH-CO2Et (in DMSO)  |
DMSO | N Param.: 15.85 sN Param.: 0.61 |
|
Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
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 |
1-(N-pyrrolidino)cyclopentene  |
dichloromethane | N Param.: 15.91 sN Param.: 0.86 |
|
Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)  |
THF | N Param.: 15.92 sN Param.: 0.72 |
|
Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 |
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 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 ethyl acetylacetate (in water)  |
water | N Param.: 15.99 sN Param.: 0.62 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of 1-phenylbutane-1,3-dione (in DMSO)  |
DMSO | N Param.: 16.03 sN Param.: 0.86 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)  |
DMSO | N Param.: 16.06 sN Param.: 0.69 |
|
Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
anion of diethyl malonate (in water)  |
water | N Param.: 16.15 sN Param.: 0.66 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
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 |
Me2S=CH-CN (in DMSO)  |
DMSO | N Param.: 16.23 sN Param.: 0.60 |
|
Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
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 |
anion of dimedone (in DMSO)  |
DMSO | N Param.: 16.27 sN Param.: 0.77 |
|
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
cyanide (in MeCN)  |
MeCN | N Param.: 16.27 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640 |
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-nitrophenyl)nitromethane (in DMSO)  |
DMSO | N Param.: 16.29 sN Param.: 0.75 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
1-(N-pyrrolidino)cyclohexene (in MeCN)  |
MeCN | N Param.: 16.42 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 16.54 sN Param.: 0.47 |
|
Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)  |
DMSO | N Param.: 16.55 sN Param.: 0.78 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
MeO-Breslow 1c  |
THF | N Param.: 16.61 sN Param.: 0.68 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
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 |
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 |
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)  |
DMSO | N Param.: 17.00 sN Param.: 0.74 |
|
Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
Desoxy Breslow intermediate 2a  |
THF | N Param.: 17.12 sN Param.: 0.80 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)  |
DMSO | N Param.: 17.19 sN Param.: 0.56 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
methoxybis(phenylsulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 17.29 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
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 |
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)  |
DMSO | N Param.: 17.36 sN Param.: 0.71 |
|
Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
Desoxy Breslow intermediate 2a  |
DMSO | N Param.: 17.41 sN Param.: 0.74 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
anion of 1,3-diphenylpropane-1,3-dione (in DMSO)  |
DMSO | N Param.: 17.46 sN Param.: 0.65 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
fluorobis(phenylsulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 17.46 sN Param.: 0.73 |
|
Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
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 |
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)  |
DMSO | N Param.: 17.52 sN Param.: 0.74 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of acetylacetone (in DMSO)  |
DMSO | N Param.: 17.64 sN Param.: 0.73 |
|
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
anion of diethyl methylmalonate (in water)  |
water | N Param.: 17.68 sN Param.: 0.50 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)  |
THF | N Param.: 17.80 sN Param.: 0.79 |
|
J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
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 |
MeSO2-CH-CO2Et (in DMSO)  |
DMSO | N Param.: 18.00 sN Param.: 0.66 |
|
Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
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 |
(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO)  |
DMSO | N Param.: 18.10 sN Param.: 0.46 |
|
Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
1,3-dimethyl-2-methyleneimidazolidine (in THF)  |
THF | N Param.: 18.11 sN Param.: 0.68 |
|
J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)  |
DMSO | N Param.: 18.19 sN Param.: 0.74 |
|
Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
anion of malononitrile (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 18.21 sN Param.: 0.69 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of dimethyl malonate (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.64 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
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 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 DMSO)  |
DMSO | N Param.: 18.31 sN Param.: 0.76 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO)  |
DMSO | N Param.: 18.32 sN Param.: 0.84 |
|
Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
anion of 3-methyl acetylacetone (in DMSO)  |
DMSO | N Param.: 18.38 sN Param.: 0.72 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
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 |
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO)  |
DMSO | N Param.: 18.50 sN Param.: 0.75 |
|
Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
(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 |
anion of ethyl cyanoacetate (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 18.59 sN Param.: 0.65 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO)  |
DMSO | N Param.: 18.63 sN Param.: 0.82 |
|
Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |