C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
(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 |
(E)-beta-(N-piperidino)styrene (in MeCN) |
MeCN | N Param.: 13.84 sN Param.: 0.73 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
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 |
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 |
(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 |
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 diethyl 2-(benzoyl)malonate (in DMSO) |
DMSO | N Param.: 13.63 sN Param.: 0.80 | | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
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 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 |
1-(N-morpholino)cyclopentene |
dichloromethane | N Param.: 13.41 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
1-(N-piperidino)cyclohexene |
dichloromethane | N Param.: 13.36 sN Param.: 0.81 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
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 p-tolylnitromethane (in water) |
water | N Param.: 13.09 sN Param.: 0.50 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
Ph3P=C(CH3)-CO2Et |
dichloromethane | N Param.: 13.09 sN Param.: 0.73 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
1-(phenylmethylamino)cyclopentene |
dichloromethane | N Param.: 12.90 sN Param.: 0.79 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
Ph3P=CH-CO2Et |
dichloromethane | N Param.: 12.79 sN Param.: 0.77 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
Desoxy Breslow intermediate 2c' |
THF | N Param.: 12.75 sN Param.: 0.71 | | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
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-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate |
MeCN | N Param.: 12.55 sN Param.: 0.92 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
1-(1-cyclohexenyl)-4-methylpiperazine |
dichloromethane | N Param.: 12.51 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 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 |
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 |
Ph3P=CH-CN |
dichloromethane | N Param.: 12.29 sN Param.: 0.75 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
(Z)-1-(N-morpholino)propene |
dichloromethane | N Param.: 12.26 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(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 |
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 |
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 |
(E)-1-(N-morpholino)propene |
dichloromethane | N Param.: 12.06 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
anion of Meldrum's acid (in water) |
water | N Param.: 12.06 sN Param.: 0.66 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
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 phenylnitromethane (in H2O) |
water | N Param.: 12.05 sN Param.: 0.53 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
1-methyl-4-(N-morpholino)tetrahydropyridine |
dichloromethane | N Param.: 12.03 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) |
DMSO | N Param.: 12.02 sN Param.: 1.17 | | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
(E)-1-(2-(4-methoxyphenyl)-1-phenylvinyl)pyrrolidine (in MeCN) |
MeCN | N Param.: 11.99 sN Param.: 0.84 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
(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 |
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)neopentylglycolborate |
MeCN | N Param.: 11.85 sN Param.: 0.72 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
anion of dimedone (in water) |
water | N Param.: 11.77 sN Param.: 0.63 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
(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 |
(E)-1-(1,2-diphenylvinyl)pyrrolidine (in MeCN) |
MeCN | N Param.: 11.66 sN Param.: 0.82 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
(E)-4-styrylmorpholine |
MeCN | N Param.: 11.66 sN Param.: 0.83 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
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 |
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 |
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 |
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 |
Desoxy Breslow intermediate 2b' |
THF | N Param.: 11.42 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
1-(N-morpholino)cyclohexene |
dichloromethane | N Param.: 11.40 sN Param.: 0.83 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN) |
MeCN | N Param.: 11.29 sN Param.: 0.76 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
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 |
anion of nitroethane (in water) |
water | N Param.: 11.25 sN Param.: 0.52 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate |
MeCN | N Param.: 11.23 sN Param.: 0.77 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
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 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 |
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 10.97 sN Param.: 0.63 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
(E)-beta-(N-morpholino)styrene |
dichloromethane | N Param.: 10.76 sN Param.: 0.87 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
1-(phenylmethylamino)cyclohexene |
dichloromethane | N Param.: 10.73 sN Param.: 0.81 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
2,4-dimethylpyrrole |
MeCN | N Param.: 10.67 sN Param.: 0.91 | | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN) |
MeCN | N Param.: 10.63 sN Param.: 0.84 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran |
dichloromethane | N Param.: 10.61 sN Param.: 0.86 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine |
MeCN | N Param.: 10.56 sN Param.: 1.01 | | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 |
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 |
diazomethane |
dichloromethane | N Param.: 10.48 sN Param.: 0.78 | | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 |
MeO-Breslow 1b |
THF | N Param.: 10.45 sN Param.: 0.81 | | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN) |
MeCN | N Param.: 10.42 sN Param.: 0.82 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
1,1-bis(trimethylsiloxy)propene |
dichloromethane | N Param.: 10.38 sN Param.: 0.87 | | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 |
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene |
dichloromethane | N Param.: 10.32 sN Param.: 0.79 | | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 |
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 |
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 |
1-butoxy-1-(trimethylsiloxy)ethene |
dichloromethane | N Param.: 10.21 sN Param.: 0.82 | | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 |
(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 |
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate |
MeCN | N Param.: 10.13 sN Param.: 0.91 | | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 |
morpholinoisobutylene |
dichloromethane | N Param.: 10.04 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
alpha-(N-morpholino)styrene |
dichloromethane | N Param.: 9.96 sN Param.: 0.79 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN) |
MeCN | N Param.: 9.94 sN Param.: 0.86 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
1,1-diethoxyethene |
dichloromethane | N Param.: 9.81 sN Param.: 0.81 | | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN) |
MeCN | N Param.: 9.64 sN Param.: 0.70 | | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 |
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 |
Ph3P=CH-COPh |
dichloromethane | N Param.: 9.54 sN Param.: 0.97 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
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 |
ethyl (E)-3-(dimethylamino)acrylate |
dichloromethane | N Param.: 9.43 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
phenyldiazomethane |
dichloromethane | N Param.: 9.35 sN Param.: 0.83 | | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 |
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) |
MeCN | N Param.: 9.25 sN Param.: 0.84 | | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h |
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) |
MeCN | N Param.: 9.23 sN Param.: 0.74 | | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 |
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 |
tetrakis(5-methyl-furan-2-yl)borate |
MeCN | N Param.: 9.09 sN Param.: 1.12 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
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 |
1-methoxy-2-methyl-1-(trimethylsiloxy)propene |
dichloromethane | N Param.: 9.00 sN Param.: 0.98 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
(trimethylsilyl)diazomethane |
dichloromethane | N Param.: 8.97 sN Param.: 0.75 | | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 |
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 8.92 sN Param.: 0.70 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
(p-bromophenyl)diazomethane |
dichloromethane | N Param.: 8.87 sN Param.: 0.82 | | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN) |
MeCN | N Param.: 8.78 sN Param.: 0.83 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
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 |
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 |
1,2,5-trimethylpyrrole |
MeCN | N Param.: 8.69 sN Param.: 1.07 | | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
Danishefskys diene |
dichloromethane | N Param.: 8.57 sN Param.: 0.84 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) |
MeCN | N Param.: 8.56 sN Param.: 0.76 | | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
ethyl (E)-3-(N-morpholino)acrylate |
dichloromethane | N Param.: 8.52 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |