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A theoretical investigation of water–solute interactions: from facial parallel to guest–host structures

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Abstract

Encapsulation of small (bio-)organic molecules within water cages is governed by a subtle equilibrium between water–water and water–solute interactions. The competition between the formation of exohedral and endohedral complexes is investigated. The first step prior to a theoretical characterization of interactions involved in such complexes lies in the judicious choice of a level of theory. The β-propiolactone (BPL), a solute for which the micro-hydration was recently characterized by means of high resolution microwave spectroscopy (Angew. Chem. 2015, 127, 993), was selected for the present study, and a calibration step is carried out. It is shown that the dispersion-corrected density functional theory (DFT-D) suitably reproduce the geometric, energetic and spectroscopic features of the BPL:(H2O)1–5 complexes. The experimentally deduced structures of the BPL:(H2O)4,5 species are fully understood in terms of the maximization of interactions between complementary sites in the MESPs. DFT-D calculations followed by the topological analysis within the Quantum Theory of Atoms in Molecules framework have shown that the solute could efficiently interact with (H2O)6,10 clusters in a similar manner that the (H2O)4,5 clusters do. The interaction of the solute with two larger water clusters is further investigated. The exohedral and endohedral BPL:(H2O)20 isomers are close in energy with each other, whereas the formation of an inclusion complex is energetically more favored than the facial interaction in the case of the BPL:(H2O)24 cluster. The topological analysis suggests that the substantial energetic stability is due to interactions between the solute and almost all oxygen atoms of the water cage.

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Acknowledgements

We thank the UPMC labex MiChem for providing Ph.D. financial support for M. Kalai. We are grateful to IDRIS for providing computer facilities (Grant No. i2016087615).

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Authors and Affiliations

  1. Sorbonne Universités, UPMC Univ. Paris 06, MONARIS, UMR 8233, Université Pierre et Marie Curie, 4 Place Jussieu, Case Courrier 49, 75252, Paris Cedex 05, France

    Cairedine Kalai, Emilie-Laure Zins & Mohammad Esmaïl Alikhani

  2. CNRS, MONARIS, UMR 8233, Université Pierre et Marie Curie, 4 Place Jussieu, Case Courrier 49, 75252, Paris Cedex 05, France

    Cairedine Kalai, Emilie-Laure Zins & Mohammad Esmaïl Alikhani

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  1. Cairedine Kalai
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  2. Emilie-Laure Zins
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Correspondence to Mohammad Esmaïl Alikhani.

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Published as part of the special collection of articles derived from the 10th Congress on Electronic Structure: Principles and Applications (ESPA-2016).

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Kalai, C., Zins, EL. & Alikhani, M.E. A theoretical investigation of water–solute interactions: from facial parallel to guest–host structures. Theor Chem Acc 136, 48 (2017). https://doi.org/10.1007/s00214-017-2074-2

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