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A computational study on the energetics and reactivity of some xanthene and thioxanthene derivatives

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Abstract

A computational study has been carried out for xanthene and thioxanthene homologous derivatives with keto, hydroxyl, carboxyl, and carboxamide functional groups on position 9, contributing to the understanding of their energetics and reactivity. For that it is presented and compared with the molecular structures, the electrostatic potential energy maps, and the electronic properties of all these heteropolycyclic compounds. The estimation of the standard molar enthalpy of formation, in the gaseous phase, at T = 298.15 K, was made only for the thioxanthydrol, thioxanthene-9-carboxylic acid, and thioxanthene-9-carboxamide using the experimental values available in the literature for the homologous compounds containing oxygen.

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Acknowledgments

This work was mainly supported by Fundação para a Ciência e a Tecnologia (FCT), Lisbon, Portugal, and European Social Fund through strategic projects PEst-C/QUI/UI0081/2011 and PEst-C/CTM/LA0011/2011 awarded to CIQUP and CICECO, respectively. VLSF thanks FCT for Ph. D. research grant SFRH/BD/41672/2007 and for the post-doctoral grant SFRH/BPD/78552/2011. JRBG holds a Ciência 2007 position of the Portuguese Ministry of Science.

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Authors and Affiliations

  1. Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, 4169-007, Porto, Portugal

    Vera L. S. Freitas & Maria D. M. C. Ribeiro da Silva

  2. CICECO, Departamento de Química, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193, Aveiro, Portugal

    José R. B. Gomes

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  1. Vera L. S. Freitas
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  2. José R. B. Gomes
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  3. Maria D. M. C. Ribeiro da Silva
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Correspondence to Maria D. M. C. Ribeiro da Silva.

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Freitas, V.L.S., Gomes, J.R.B. & Ribeiro da Silva, M.D.M.C. A computational study on the energetics and reactivity of some xanthene and thioxanthene derivatives. Struct Chem 24, 661–670 (2013). https://doi.org/10.1007/s11224-012-0117-9

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  • DOI: https://doi.org/10.1007/s11224-012-0117-9

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