C-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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-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-(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-(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-(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-(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-(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-amino-indole  |
MeCN | N Param.: 7.22 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-bromo-indole  |
MeCN | N Param.: 4.38 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-chloro-indole  |
MeCN | N Param.: 4.42 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-hydroxy-indole  |
MeCN | N Param.: 6.44 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 |
5-methoxy-indole  |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methyl-2,3-dihydrofuran (in MeCN)  |
MeCN | N Param.: 7.65 sN Param.: 0.86 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
5-methyl-indole  |
MeCN | N Param.: 6.00 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
6,6-dimethylfulvene  |
MeCN | N Param.: 3.93 sN Param.: 0.88 |
|
Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (in MeCN)  |
MeCN | N Param.: 2.81 sN Param.: 0.57 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
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 |
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 |
7-azaindole  |
MeCN | N Param.: 3.87 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
8-(benzyloxy)-2,2-di-tert-butyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline  |
dichloromethane | N Param.: 1.85 sN Param.: 1.28 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
8-(benzyloxy)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine  |
dichloromethane | N Param.: 1.94 sN Param.: 1.24 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
allyl-tert.butyl-dimethylsilane  |
dichloromethane | N Param.: 1.80 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 |
allyltri-n-butylsilane  |
dichloromethane | N Param.: 2.09 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 |
allyltriethylsilane  |
dichloromethane | N Param.: 1.93 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 |
allyltriisopropylsilane  |
dichloromethane | N Param.: 2.04 sN Param.: 0.95 |
|
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 |
allyltriphenylgermane  |
dichloromethane | N Param.: 1.20 sN Param.: 0.90 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriphenylsilane  |
dichloromethane | N Param.: -0.13 sN Param.: 1.21 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltriphenylstannane  |
dichloromethane | N Param.: 3.09 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltris(trimethylsilyl)silane  |
dichloromethane | N Param.: 1.95 sN Param.: 0.98 |
|
Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
alpha-(N-morpholino)styrene  |
dichloromethane | N Param.: 9.96 sN Param.: 0.79 |
|
Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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-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-(pentamethyldisilyl)styrene  |
dichloromethane | N Param.: 0.61 sN Param.: 1.01 |
|
Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
alpha-(trimethylsilyl)styrene  |
dichloromethane | N Param.: -1.13 sN Param.: 1.46 |
|
Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
alpha-methylstyrene  |
dichloromethane | N Param.: 2.35 sN Param.: 1.00 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
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 (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 water)  |
water | N Param.: 14.25 sN Param.: 0.46 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
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-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-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 |