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Journal of Molecular Modeling

, Volume 19, Issue 5, pp 1985–1994 | Cite as

Effect of stepwise microhydration on the methylammonium···phenol and ammonium···phenol interaction

  • Ana A. Rodríguez-Sanz
  • J. Carrazana-García
  • Enrique M. Cabaleiro-LagoEmail author
  • Jesús Rodríguez-Otero
Original Paper

Abstract

A computational study has been performed for studying the characteristics of the interaction of phenol with ammonium and methylammonium cations. The effect of the presence of water molecules has also been considered by microhydrating the clusters with up to three water molecules. Clusters of phenol with ammonium and methylammonium cations present similar characteristics, though ammonium complexes have been found to be more stable than the methylammonium ones. The first water molecule included in the complexes interacts with a N-H group of ammoniun cations and simultaneously with the hydroxyl oxygen atom of phenol (or the aromatic ring). This first water molecule is more tightly bound in the complex, so the stability gain as more water molecules are included drops significantly by 2-3 kcal mol−1 with respect to the first one. As more water molecules are included, the differences between favorable coordination sites (the cation, the hydroxyl group or a previous water molecule) decrease. As a consequence, several of the most stable complexes located including three water molecules already exhibit hydrogen bonds between the hydroxyl group and one water molecule. The results indicate that a cyclic pattern formed by a series of hydrogen bonds: π···H-N-H···O-H···O-ϕ, is characteristic of the most stable minima, being kept as more water molecules are included in the system. Therefore, this pattern can be expected to be crucial in ammonium cations···phenol interaction if exposed to the solvent to any degree.

Keywords

Ab initio calculation Cation···π interactions Microhydration Non-covalent interactions Solvent effects 

Notes

Acknowledgments

The authors thank the financial support from the Ministerio de Ciencia e Innovación and the ERDF 2007–2013 (Grant No. CTQ2009-12524). We are also thankful to the Centro de Supercomputación de Galicia (CESGA) for the use of their computers. A. A. R.-S. also thanks Spanish Ministerio Ciencia e Innovación for a FPI grant.

Supplementary material

894_2012_1579_MOESM1_ESM.doc (3.6 mb)
ESM 1 (DOC 3640 kb)

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Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Ana A. Rodríguez-Sanz
    • 1
  • J. Carrazana-García
    • 1
  • Enrique M. Cabaleiro-Lago
    • 1
    Email author
  • Jesús Rodríguez-Otero
    • 2
  1. 1.Departamento de Química Física, Facultade de CienciasUniversidade de Santiago de CompostelaLugoSpain
  2. 2.Departamento de Química Física, Facultade de QuímicaUniversidade de Santiago de CompostelaSantiago de CompostelaSpain

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