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Topological insights into the 1/1 diacetyl/water complex gained using a new methodological approach

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Abstract

The 1/1 diacetyl/water complex is of atmospheric relevance. Previous experimental and theoretical studies have focused on two isomeric forms, and geometry optimizations were carried out on them. Herein, we propose a six-step methodological approach based on topological properties to search for and characterize all of the isomeric forms of the 1/1 noncovalent diacetyl/water complex: (1) a molecular electrostatic potential (MESP) study to get an overview of the V min and V max regions on the molecular surfaces of the separate molecules (diacetyl and water); (2) a topological (QTAIM and ELF) study allowing thorough characterization of the electron densities (QTAIM) and irreducible ELF basins of the separate molecules; (3) full optimization of the predicted structures based on the interaction between complementary reaction sites; (4) energetic characterization based on a symmetry-adapted perturbation theory (SAPT) analysis; (5) topological characterization of the optimized complexes; (6) analysis of the complexes in terms of orbital overlaps (natural bond orbitals, NBO analysis). Using this approach, in addition to achieving the topological characterization of the two isomeric forms already reported, a third possible isomer was identified and characterized.

Topological tools to study monohydrated complexes

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Scheme 1A–B
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Notes

  1. For a discussion of how the energies of intramolecular hydrogen bonds can be estimated, see for example [14].

  2. See also [60].

  3. See the ESM at http://dx.doi.org/xxxxx to view the Cartesian coordinates of the monomers and the isomers S1, S2, and S3 of the 1/1 DAC/water complex optimized at both the MP2/AVTZ and CCSD(T)-F12/AVDZ levels of theory.

  4. We further investigated the reason for this particular location of the BCP, and an article is in preparation on this topic, in line with Shahbazian’s work. See for instance [68–70].

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Authors and Affiliations

  1. Sorbonne Universités, UPMC Univ. Paris 06, MONARIS, UMR 8233, Université Pierre et Marie Curie, Pr. M. Esmaïl Alikhani CC 49, 4 place Jussieu, 75252, Paris, France

    D. Dargent, E. L. Zins, B. Madebène & M. E. Alikhani

  2. CNRS, MONARIS, UMR 8233, Université Pierre et Marie Curie, 4 Place Jussieu, case courrier 49, F-75252, Paris Cedex 05, France

    D. Dargent, E. L. Zins, B. Madebène & M. E. Alikhani

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  1. D. Dargent
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  2. E. L. Zins
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Correspondence to M. E. Alikhani.

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Dargent, D., Zins, E.L., Madebène, B. et al. Topological insights into the 1/1 diacetyl/water complex gained using a new methodological approach. J Mol Model 21, 214 (2015). https://doi.org/10.1007/s00894-015-2751-9

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