TABLE 2.
General compound group | Substrate | Relative activity (%)a |
---|---|---|
Benzene derivatives | Benzonitrile | 100 |
4-Aminobenzonitrile | 28 | |
Benzylcyanide | 52 | |
2-Chlorobenzylcyanide | 6 | |
3-Chlorobenzylcyanide | 316 | |
4-Chlorobenzylcyanide | 11 | |
2-Methylbenzylcyanide | 207 | |
4-Hydroxybenzylcyanide | 10 | |
2-3 Ring systems | 2-Naphthalenecarbonitrile | 757 |
2-Naphthaleneacetonitrile | 8 | |
9-Anthracenecarbonitrile | 10 | |
3-Phenoxyphenylacetonitrile | 35 | |
Heterocyclic compounds | 2-Thienylacetonitrile | 311 |
3-Thienylacetonitrile | 102 | |
3-Cyanopyridine | 245 | |
Indole-3-acetonitrile | 354 | |
Saturated aliphatic mononitriles | Propionitrile | 33 |
2-Chloropropionitrile | 270 | |
3-Dimetylaminopropionitrile | 8 | |
Butyronitrile | 109 | |
Valeronitrile | 222 | |
Isovaleronitrile | 9 | |
2-Methylglutaronitrile | 394 | |
Octanoic acid nitrile | 303 | |
Dodecanoic acid nitrile | 36 | |
Saturated aliphatic dinitriles | Adipinic acid dinitrile | 528 |
Octanoic acid dinitrile | 588 | |
Decanoic acid dinitrile | 476 | |
Unsaturated aliphatic mononitriles | Acrylonitrile | 68 |
2-Butenenitrile | 49 | |
3-Butenenitrile | 409 | |
Unsaturated aliphatic dinitriles | Fumarodinitrile | 12,000 |
3-Hexenoic acid dinitrile | 14 |
The activity with benzonitrile was 100%. Less than 5% relative activity was found with the following substrates. 2-Ethyl-2-phenylbutyronitrile, 2-phenylvaleronitrile, 2,6-dichlorobenzylcyanide, naproxen nitrile, ketoprofen nitrile, acetonitrile, malononitrile, 2-methyl-3-butenenitrile, diethyldicyanofumarate, isobutyronitrile, 2-methylbutyronitrile, pentadecanenitrile, and nonadecanenitrile.