C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(allyl)dicarbonyl(cyclopentadienyl)iron(II)  |
dichloromethane | N Param.: 6.78 sN Param.: 0.95 |  | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 |
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II) |
dichloromethane | N Param.: 8.45 sN Param.: 0.83 | | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 |
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 |
anion of nitroethane (in 91M9AN) |
MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.67 | | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
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 phenylnitromethane (in 91M9AN) |
MeOH-MeCN mix | N Param.: 12.51 sN Param.: 0.67 | | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of p-tolylnitromethane (in 91M9AN) |
MeOH-MeCN mix | N Param.: 13.58 sN Param.: 0.64 | | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
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 (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 |
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 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 |
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 |
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 |
5-chloro-2-methylindole |
MeCN | N Param.: 6.08 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
4-methoxy-indole |
MeCN | N Param.: 5.41 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
7-azaindole |
MeCN | N Param.: 3.87 sN Param.: 1.10 | | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
tert-butyl isocyanide |
dichloromethane | N Param.: 5.47 sN Param.: 0.77 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
benzyl isocyanide |
dichloromethane | N Param.: 4.90 sN Param.: 0.74 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
2,6-dimethylphenyl isocyanide |
dichloromethane | N Param.: 4.59 sN Param.: 0.87 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
p-tosylmethyl isocyanide (TosMIC) |
dichloromethane | N Param.: 3.50 sN Param.: 0.76 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
4-cyanophenyl isocyanide |
dichloromethane | N Param.: 3.57 sN Param.: 0.72 | | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
anisole |
dichloromethane | N Param.: -1.18 sN Param.: 1.20 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
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 |
bis(4-nitrophenyl)methanide (in DMSO) |
DMSO | N Param.: 19.92 sN Param.: 0.67 | | ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...] |
2,5-dimethylpyrrole |
MeCN | N Param.: 8.01 sN Param.: 0.96 | | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
1,2,5-trimethylpyrrole |
MeCN | N Param.: 8.69 sN Param.: 1.07 | | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
2,4-dimethylpyrrole |
MeCN | N Param.: 10.67 sN Param.: 0.91 | | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
3-ethyl-2,4-dimethylpyrrole |
MeCN | N Param.: 11.63 sN Param.: 0.95 | | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
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-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 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-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-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 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-(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 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 |
azulene |
MeCN | N Param.: 6.66 sN Param.: 1.02 | | 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 |
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-(julolidin-9-yl)fulvene |
MeCN | N Param.: 7.79 sN Param.: 1.06 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
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 |
dichloromethane | N Param.: 11.95 sN Param.: 0.76 | | Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 |
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 |
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 |
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 |
MeSO-CH-CO2Et (in DMSO) |
DMSO | N Param.: 20.61 sN Param.: 0.64 | | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
(cyclohexen-1-yl)prolinate (in MeCN) |
MeCN | N Param.: 18.86 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
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 |
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 |
(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 |
allyltris(trimethylsilyl)silane |
dichloromethane | N Param.: 1.95 sN Param.: 0.98 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
(2-methylallyl)tris(trimethylsilyl)silane |
dichloromethane | N Param.: 4.63 sN Param.: 0.87 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
2-(tris(trimethylsilyl)siloxy)propene |
dichloromethane | N Param.: 6.04 sN Param.: 0.82 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
1-(tris(trimethylsilyl)siloxy)cyclohexene |
dichloromethane | N Param.: 5.07 sN Param.: 0.91 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
(tris(trimethylsilyl)siloxy)ethene |
dichloromethane | N Param.: 4.01 sN Param.: 0.83 | | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 21.72 sN Param.: 0.45 | | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF) |
THF | N Param.: 23.35 sN Param.: 0.40 | | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
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 |
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 |
(5-methyl-furan-2-yl) pinacol boronate |
MeCN | N Param.: 2.90 sN Param.: 0.98 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(5-methyl-furan-2-yl) MDA boronate |
MeCN | N Param.: 6.38 sN Param.: 0.86 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(5-methyl-furan-2-yl) MIDA boronate |
MeCN | N Param.: 1.84 sN Param.: 1.26 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(5-methyl-furan-2-yl) trifluoroborate |
MeCN | N Param.: 7.66 sN Param.: 1.04 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |