The role of nonbonded sulfur-oxygen interaction in the dissociative electron transfer to nitro-substituted arenesulfenyl chlorides

Journal of the American Chemical Society
Chang JiAbdelaziz Houmam

Abstract

The electrochemical reduction of p-nitrophenyl sulfenyl chloride, o-nitrophenyl sulfenyl chloride as well as bis(4-nitrophenyl) disulfide and bis(2-dinitrophenyl) disulfide was investigated in acetonitrile at an inert electrode. Reduction standard potentials as well standard heterogeneous electron-transfer rate constants have been determined using convolution analysis. An unexpected big difference in the thermodynamics and kinetics of the initial electron-transfer process as well as a striking change in the reductive cleavage mechanism of the S-Cl bond as a function of the nitro group position on the aryl ring of the aryl sulfenyl chloride is observed. A computational study at the B3LYP level shows that this difference in behavior is due to the through-space nonbonded S...O interaction in the o-nitrophenyl sulfenyl chloride.

References

Jul 18, 2001·Journal of the American Chemical Society·A Godsk LarsenK Daasbjerg
Oct 16, 2003·Journal of the American Chemical Society·Abdelaziz HoumamAdrian L Schwan
Dec 3, 2003·Journal of the American Chemical Society·Sabrina AntonelloFlavio Maran

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Citations

Oct 6, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Abdelaziz HoumamKallum M Koczkur
Mar 23, 2017·Chemical Communications : Chem Comm·R Alex MayoKathryn E Preuss
Oct 18, 2012·Chemical Communications : Chem Comm·Abdelaziz Houmam, Emad M Hamed
Nov 30, 2006·Journal of the American Chemical Society·Chang JiAbdelaziz Houmam

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