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The structure and energetics of pyrrolidinones, tetrahydrofuranones, piperidinones, and tetrahydropyranones: a computational study

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Abstract

We have performed high level ab initio quantum chemical calculations for 2- and 3-pyrrolidinone; tetrahydro-2- and -3-furanone; 2-, 3-, and 4-piperidinone; and tetrahydro-2-, -3-, and -4-pyranone. The most stable molecular structures were obtained from DFT calculations using the B3LYP density functional and the 6-31G(d) and 6-311+G(3df,2p) basis sets. The respective enthalpies of formation have been computed by the G3(MP2)//B3LYP composite method and appropriately chosen reactions. The calculated results are in excellent agreement with experimental data reported in the literature.

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Acknowledgments

M. S. Miranda thanks Fundação para a Ciência e a Tecnologia, FCT, Lisbon, Portugal, for the financial support under the frame of the Ciência 2008 program.

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Authors and Affiliations

  1. Centro de Geologia da Universidade do Porto, Rua do Campo Alegre, s/n, 4169-007, Porto, Portugal

    Margarida S. Miranda

  2. Departamento de Química e Bioquímica, Centro de Investigação em Química, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, s/n, 4169-007, Porto, Portugal

    Joaquim C. G. Esteves da Silva

  3. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD, 21250, USA

    Chi Hon, Steven J. McKerrall & Joel F. Liebman

Authors
  1. Margarida S. Miranda
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  2. Joaquim C. G. Esteves da Silva
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  3. Chi Hon
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  4. Steven J. McKerrall
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  5. Joel F. Liebman
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Correspondence to Margarida S. Miranda or Joel F. Liebman.

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Special Issue in honor of Prof. Maria Victoria Roux.

This paper is dedicated to our friend and colleague Maria Victoria Roux on the occasion of her official retirement.

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Miranda, M.S., da Silva, J.C.G.E., Hon, C. et al. The structure and energetics of pyrrolidinones, tetrahydrofuranones, piperidinones, and tetrahydropyranones: a computational study. Struct Chem 24, 1829–1839 (2013). https://doi.org/10.1007/s11224-013-0237-x

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  • DOI: https://doi.org/10.1007/s11224-013-0237-x

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