131089-01-5Relevant academic research and scientific papers
Side Chain Hydroxylation of Aromatic Compounds by Fungi. Part 4. Influence of the para Substituent on Kinetic Isotope Effects During Benzylic Hydroxylation by Mortierella isabellina
Holland, Herbert L.,Brown, Frances M.,Conn, Morgan
, p. 1651 - 1655 (2007/10/02)
The benzylic hydroxylation of a series of para-substituted toluenes by the fungus Mortierella isabellina has been studied by using CD3, CHD2, and CH2D methyl labelled substrates.Inter- and intramolecular primary and secondary deuterium kinetic isotope effect ratios have been determined: the intermolecular primary effects are maximal with strongly electron-withdrawing para substituents (R = CN and CF3), while the intramolecular primary effects are minimal for R = H but increase in instances where R is electron donating or withdrawing.These results are interpreted in terms of a dependence of the hydroxylation mechanism on the nature of the para substituent.
