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Structural Chemistry

, Volume 30, Issue 1, pp 237–245 | Cite as

Density functional theory study of the oxidation reaction in the gas and aqueous phase of allyl methyl disulfide with hydroxyl radical

  • Mario G. Díaz
  • Matías F. Andrada
  • Esteban G. Vega-Hissi
  • Juan C. Garro MartinezEmail author
Original Research
  • 40 Downloads

Abstract

An in silico analysis of the oxidation mechanism of allyl methyl disulfide (AMDS) by hydroxyl radical was achieved at DFT level using B3LYP, CAM-B3LYP, M06-2X, and BMK functionals and 6-311++G(3df,2p) triple-zeta basis set. The calculations were carried out in both gas and aqueous phases using the SMD model (density-based solvation model). Three potential reactions were proposed according to results of Fukui function; in reactions 1 and 2, the hydroxyl radical attacks the sulfur atom breaking the disulfide bond and the reaction 3 is a hydrogen atom subtraction reaction. The respective structures of transition states (TSs) were found. Intrinsic reaction coordinate (IRC) calculations were performed for the three reactions, and their rates and equilibrium constants were calculated. When the solvent effect is taken into account, the four DFT functionals employed designate R3 (a subtraction reaction) as the fastest reaction. Thus, we elucidated the thermodynamic and kinetic feasibility of the proposed oxidation reactions.

Keywords

Reactive oxygen species Allyl methyl disulfide Hydroxyl radical Density functional theory Intrinsic reaction coordinates 

Notes

Acknowledgments

Mario G. Díaz gratefully acknowledges a doctoral fellowship from CONICET.

Funding information

This study is financially supported by the UNSL and CONICET.

Compliance with ethical standards

Conflicts of interest

The authors declare that they have no conflict of interest.

Supplementary material

11224_2018_1198_MOESM1_ESM.docx (5 mb)
ESM 1 Supplementary material contains the Fig.1S related Molecular structure of optimized TSs in gas phase. (DOCX 5163 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Mario G. Díaz
    • 1
  • Matías F. Andrada
    • 2
  • Esteban G. Vega-Hissi
    • 1
  • Juan C. Garro Martinez
    • 1
    Email author
  1. 1.IMIBIO, CONICET, Facultad de Química, Bioquímica y FarmaciaUniversidad Nacional de San LuisSan LuisArgentina
  2. 2.Facultad de Química, Bioquímica y FarmaciaUniversidad Nacional de San LuisSan LuisArgentina

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