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Hydrogen Bond Between the α-Hydroxycarboxyl, α-Hydroxyester and α-Hydroxyamide Groups: Ab Initio Gas-Phase and Solution Study of a Double Linkage via the Hydroxyl Group

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Quantum Systems in Chemistry and Physics Volume 2

Part of the book series: Progress in Theoretical Chemistry and Physics ((PTCP,volume 2/3))

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Abstract

The results of studies on hydrogen bonded dimers which involve hydroxyl group acting as both a donor and acceptor in an intermolecular hydrogen bonding are presented. Systems formed by α-hydroxy-COX moieties, where X is OH, NH2 or OCH3, have been investigated in the gas-phase and in solution and compared with analogous patterns observed in crystals. The RHF/6-311++G** level of theory has been employed to compute energies and optimise geometries in the isolated state. The Polarisable Continuum Model with the same basis set has been employed to include the solvation effects. Correlation corrections at the MP2 level and zero-point corrections at the HF level have been calculated in order to verify the energy differences between conformers. In summary, it has been found that hydroxyl group may be regarded as complementary to the α-hydroxy-COX group and most of such arrangements are stable not only in the isolated state but also in liquid media, particularly in a polar one.

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Authors and Affiliations

  1. Quantum Chemistry Group, Adam Mickiewicz University, Grunwaldzka 6, 60-780, Poznań, Poland

    Agnieszka Szarecka & Jacek Rychlewski

  2. Institute of Bioorganic Chemistry, Polish Academy of Sciences, PCSS, Noskowskiego 12/14, 61-704, Poznań, Poland

    Jacek Rychlewski

  3. Department of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780, Poznań, Poland

    Urszula Rychlewska

Authors
  1. Agnieszka Szarecka
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  2. Jacek Rychlewski
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  3. Urszula Rychlewska
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Editor information

Editors and Affiliations

  1. Estación Experimental del Zaidín (C.S.I.C.), Granada, Spain

    Alfonso Hernández-Laguna

  2. Laboratoire de Chimie Physique (C.N.R.S.), Paris, France

    Jean Maruani

  3. Universita di Pisa, Pisa, Italy

    Roy McWeeny

  4. Rutherford Appleton Laboratory, Oxfordshire, UK

    Stephen Wilson

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© 2000 Kluwer Academic Publishers

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Szarecka, A., Rychlewski, J., Rychlewska, U. (2000). Hydrogen Bond Between the α-Hydroxycarboxyl, α-Hydroxyester and α-Hydroxyamide Groups: Ab Initio Gas-Phase and Solution Study of a Double Linkage via the Hydroxyl Group. In: Hernández-Laguna, A., Maruani, J., McWeeny, R., Wilson, S. (eds) Quantum Systems in Chemistry and Physics Volume 2. Progress in Theoretical Chemistry and Physics, vol 2/3. Springer, Dordrecht. https://doi.org/10.1007/0-306-48145-6_19

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  • DOI: https://doi.org/10.1007/0-306-48145-6_19

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-7923-5970-8

  • Online ISBN: 978-0-306-48145-1

  • eBook Packages: Springer Book Archive

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