Electronic effects of para-substitution on acetophenones in the reaction of rat liver 3α-hydroxysteroid dehydrogenase was written by Uwai, Koji;Konno, Noboru;Yasuta, Yuka;Takeshita, Mitsuhiro. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Formula: C9H9NO This article mentions the following:
Stereoselective reductive metabolism of various p-substituted acetophenone derivatives was studied using isolated rat liver 3α-hydroxysteroid dehydrogenase (3α-HSD). Kinetic experiments were performed and analyzed by measuring the products by HPLC using a chiral column. The results demonstrated that the presence of an electron-withdrawing substituent on the benzene ring plays an important role in determining the reduction rate in the syntheses of various (S)-alcs. from their corresponding carbonyl compounds A plot of log {(Vmax/Km)X/(Vmax/Km)H} vs. the substituent parameter (π, σpara, Es) shows an increasing rate mainly for electron-withdrawing substituents, with a correlation coefficient (r2) of 0.97 which was obtained for triplicate data that were significant at the p < 0.0001 level. With this in mind, new drugs can be designed that exploit this reduction pathway by introducing an electron-withdrawing group adjacent to the reduction site when a reduction reaction is desired, or by adding an electron-donating group when minimization of the reduction pathway is desired. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).
(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Formula: C9H9NO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts