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Computational investigation of the formation and isomerization pathways of CH3SNO2 and the S–N bond dissociation energies of CH3S(O) n NO2 (n = 0, 1, 2) species

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Abstract

Ab initio and density functional theory (DFT) calculations are employed to investigate the formation and isomerization pathways of methyl thionitrate, CH3SNO2, and the S–N bond dissociation energies (BDE) of the sulfonated methyl thionitrates of the type CH3S(O) n NO2 (n = 0, 1, 2). The calculations indicate that CH3SNO2 may be formed as a stabilized by-product in the reaction CH3S + NO2 which mainly leads to CH3SO + NO. In general, the compounds of the type CH3S(O) n NO2 (n = 0, 1, 2) may be formed as bound intermediates in the homologous reactions CH3S(O) n  + NO2. The calculated S–N BDE exhibit an interesting dependence on the number of the sulfonic oxygen atoms present in each species.

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Acknowledgments

This research has been co-financed by the European Union (European Social Fund—ESF) and Greek national funds through the Operational Program “Education and Lifelong Learning” of the National Strategic Reference Framework (NSRF)—Research Funding Program: Heracleitus II. Investing in knowledge society through the European Social Fund. Computer services provided by the Center of Molecular Simulations of the University of Ioannina are gratefully acknowledged.

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  1. Physical Chemistry Sector, Department of Chemistry, University of Ioannina, 45110, Ioannina, Greece

    Zoi Salta & Agnie M. Kosmas

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  1. Zoi Salta
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  2. Agnie M. Kosmas
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Correspondence to Agnie M. Kosmas.

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Salta, Z., Kosmas, A.M. Computational investigation of the formation and isomerization pathways of CH3SNO2 and the S–N bond dissociation energies of CH3S(O) n NO2 (n = 0, 1, 2) species. Struct Chem 27, 1149–1156 (2016). https://doi.org/10.1007/s11224-015-0737-y

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  • DOI: https://doi.org/10.1007/s11224-015-0737-y

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