C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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-(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 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 acetylacetone (in water) |
water | N Param.: 13.73 sN Param.: 0.64 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
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 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 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-nitrobenzyl-CN (in DMSO) |
DMSO | N Param.: 19.67 sN Param.: 0.68 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
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-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-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-cyanobenzyl-CN (in DMSO) |
DMSO | N Param.: 25.11 sN Param.: 0.54 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
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-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-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-CN (in DMSO) |
DMSO | N Param.: 27.28 sN Param.: 0.50 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
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-(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 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 |
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 |
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 |
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 |
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-propionitrile (in DMSO) |
DMSO | N Param.: 28.95 sN Param.: 0.58 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
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 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 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 91M9AN) |
MeOH-MeCN mix | N Param.: 12.20 sN Param.: 0.71 | | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
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 2-(4-NO2-C6H4)propionitrile (in DMSO) |
DMSO | N Param.: 19.61 sN Param.: 0.60 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 2-(4-CN-C6H4)propionitrile (in DMSO) |
DMSO | N Param.: 25.35 sN Param.: 0.56 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 1-phenylpropan-2-one (in DMSO) |
DMSO | N Param.: 24.99 sN Param.: 0.60 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
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 |
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 |
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 |
anion of 1,2-diphenylethanone (in DMSO) |
DMSO | N Param.: 23.15 sN Param.: 0.60 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
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 |
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 (benzylsulfonyl)benzene (in DMSO) |
DMSO | N Param.: 25.77 sN Param.: 0.56 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
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 |
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 |
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 (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 |
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 |
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 |
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO) |
DMSO | N Param.: 22.60 sN Param.: 0.57 | | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO) |
DMSO | N Param.: 24.30 sN Param.: 0.51 | | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
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 (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 |
alpha-methylstyrene |
dichloromethane | N Param.: 2.35 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
alpha-(trimethylsilyl)styrene |
dichloromethane | N Param.: -1.13 sN Param.: 1.46 | | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
alpha-(pentamethyldisilyl)styrene |
dichloromethane | N Param.: 0.61 sN Param.: 1.01 | | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
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 |
alpha-(N-morpholino)styrene |
dichloromethane | N Param.: 9.96 sN Param.: 0.79 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
allyltris(trimethylsilyl)silane |
dichloromethane | N Param.: 1.95 sN Param.: 0.98 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
allyltriphenylstannane |
dichloromethane | N Param.: 3.09 sN Param.: 0.90 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltriphenylsilane |
dichloromethane | N Param.: -0.13 sN Param.: 1.21 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltriphenylgermane |
dichloromethane | N Param.: 1.20 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltrimethylsilane |
dichloromethane | N Param.: 1.68 sN Param.: 1.00 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
allyltriisopropylsilane |
dichloromethane | N Param.: 2.04 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltrihexylsilane |
dichloromethane | N Param.: 2.11 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriethylsilane |
dichloromethane | N Param.: 1.93 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltributylstannane |
dichloromethane | N Param.: 5.46 sN Param.: 0.89 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltri-n-butylsilane |
dichloromethane | N Param.: 2.09 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allylchlorodimethylsilane |
dichloromethane | N Param.: -0.57 sN Param.: 1.06 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
allyl-tert.butyl-dimethylsilane |
dichloromethane | N Param.: 1.80 sN Param.: 0.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
7-azaindole |
MeCN | N Param.: 3.87 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
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 |
6-(julolidin-9-yl)fulvene |
MeCN | N Param.: 7.79 sN Param.: 1.06 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-(4-dimethylamino-phenyl)fulvene |
MeCN | N Param.: 6.72 sN Param.: 0.87 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6,6-dimethylfulvene |
MeCN | N Param.: 3.93 sN Param.: 0.88 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
5-methyl-indole |
MeCN | N Param.: 6.00 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methoxy-indole |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 | | 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 |
5-hydroxy-indole |
MeCN | N Param.: 6.44 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 |
5-chloro-indole |
MeCN | N Param.: 4.42 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-2-methylindole |
MeCN | N Param.: 6.08 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-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 |
5-amino-indole |
MeCN | N Param.: 7.22 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 8.16 sN Param.: 0.67 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
5-(triphenylsiloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 11.28 sN Param.: 0.91 | | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
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 |
5-(trimethylsiloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 12.56 sN Param.: 0.70 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF) |
THF | N Param.: 31.92 sN Param.: 0.52 | | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) |
DMSO | N Param.: 13.79 sN Param.: 0.86 | | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
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 |
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 |
4-methyl-penta-1,3-diene |
dichloromethane | N Param.: 2.60 sN Param.: 1.00 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide |
dichloromethane | N Param.: 3.85 sN Param.: 0.84 | | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran |
dichloromethane | N Param.: 11.50 sN Param.: 0.91 | | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 |
4-methoxy-indole |
MeCN | N Param.: 5.41 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
4-cyanophenyl isocyanide |
dichloromethane | N Param.: 3.57 sN Param.: 0.72 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6 |
dichloromethane | N Param.: -1.11 sN Param.: 0.92 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |