Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
ethanolate (in ethanol)![]() ![]() |
EtOH | N Param.: 15.78 sN Param.: 0.65 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
91% ethanol/9% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 7.10 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
80% ethanol/20% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.94 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
67% ethanol/33% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.74 sN Param.: 0.89 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
50% ethanol/50% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.37 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
33% ethanol/67% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.06 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
20% ethanol/80% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 5.77 sN Param.: 0.92 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
10% ethanol/90% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 5.19 sN Param.: 0.96 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
ethanolate (in 91E9AN)![]() ![]() |
EtOH-MeCN mix | N Param.: 16.08 sN Param.: 0.62 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
azide ion (in 91E9AN)![]() ![]() |
EtOH-MeCN mix | N Param.: 16.30 sN Param.: 0.73 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
chloride (in hexafluoroisopropanol)![]() ![]() |
HFIP | N Param.: 8.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
isopropanolate (in propan-2-ol)![]() ![]() |
iPrOH | N Param.: 17.03 sN Param.: 0.63 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
91% propan-2-ol/9% MeCN (v/v)![]() ![]() |
iPrOH-MeCN mix | N Param.: 6.49 sN Param.: 0.96 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
isopropanolate (in 91iPr9AN)![]() ![]() |
iPrOH-MeCN mix | N Param.: 17.71 sN Param.: 0.58 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
azide ion (in 91iPr9AN)![]() ![]() |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
cyanide (in MeCN)![]() ![]() |
MeCN | N Param.: 16.27 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640 | |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 17.94 sN Param.: 0.60 | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u | |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 12.13 sN Param.: 0.60 | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u | |
chloride (in MeCN)![]() ![]() |
MeCN | N Param.: 17.20 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
nitrite ion (in MeCN)![]() ![]() |
MeCN | N Param.: 17.20 sN Param.: 0.72 | Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274 | |
4-(dimethylamino)pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 15.51 sN Param.: 0.62 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
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 | |
4-chloroaniline (in MeCN)![]() ![]() |
MeCN | N Param.: 12.92 sN Param.: 0.60 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
aniline (in MeCN)![]() ![]() |
MeCN | N Param.: 12.64 sN Param.: 0.68 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
p-toluidine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.19 sN Param.: 0.69 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
4-methoxyaniline (in MeCN)![]() ![]() |
MeCN | N Param.: 13.42 sN Param.: 0.73 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
DABCO (in MeCN)![]() ![]() |
MeCN | N Param.: 18.80 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 | |
quinuclidine (in MeCN)![]() ![]() |
MeCN | N Param.: 20.54 sN Param.: 0.60 | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 | |
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 | |
DBU (in MeCN)![]() ![]() |
MeCN | N Param.: 15.29 sN Param.: 0.70 | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a | |
DBN (in MeCN)![]() ![]() |
MeCN | N Param.: 16.28 sN Param.: 0.67 | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a | |
cyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 13.60 sN Param.: 0.84 | Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 | |
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 |



















































