Journal of the American Chemical Society 2003-10-22

Regioselective bond cleavage in the dissociative electron transfer to benzyl thiocyanates.

Abdelaziz Houmam, Emad M Hamed, Philippe Hapiot, John M Motto, Adrian L Schwan

Index: J. Am. Chem. Soc. 125(42) , 12676-7, (2003)

Full Text: HTML

Abstract

The electrochemical reduction of benzyl thiocyanate and p-nitrobenzyl thiocyanate was investigated in acetonitrile at an inert electrode. These two compounds reveal a change in the reductive cleavage mechanism, and more interestingly, they show a clear-cut example of a regioselective bond dissociation. Both phenomena may be understood on the basis of the dissociative ET theory and its extension to the formation/dissociation reactions of radical ions. While the effect of the standard oxidation potential of the leaving group seems to be predominant in understanding the change in the ET mechanism by changing the driving force, the regioselective cleavage is dictated by changes in the intrinsic barrier related to the nature of the substituent on the aryl moiety.

Related Compounds

  • benzyl thiocyanate

Related Articles:

In vitro metabolic conversion of the organic breakdown products of glucosinolate to goitrogenic thiocyanate anion.

2015-08-30

[J. Sci. Food Agric. 95 , 2244-51, (2015)]

Subcellular localization of enzymes in Streptomyces aureofaciens and its alteration by benzyl thiocyanate. I. Phosphatases and ATP-glucokinase.

1987-01-01

[Folia Microbiol. (Praha) 32(5) , 402-10, (1987)]

Protein profiles of Streptomyces aureofaciens producing tetracyclines: reappraisal of the effect of benzyl thiocyanate.

1995-08-01

[Curr. Microbiol. 31(2) , 84-91, (1995)]

Effect of some benzyl thiocyanate analogs on tetracycline production.

1987-09-01

[J. Antibiot. 40(9) , 1341-3, (1987)]

Effects of dietary compounds on alpha-hydroxylation of N-nitrosopyrrolidine and N'-nitrosonornicotine in rat target tissues.

1984-07-01

[Cancer Res. 44(7) , 2924-2928, (1984)]

More Articles...