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Exploring heterocyclic cations ability to form the iodide–iodine halogen bond: case study of chalcogenazolo(ino)quinolinium crystals

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Abstract

Analysis of iodine-derived chalcogenazolo(ino)quinolinium mono- and triiodides shows that the covalently bonded iodine atoms in the fragments C(sp2)–I and C(sp3)–I differ significantly in iodide–iodine halogen bonding ability. The local and integrated characteristics of kinetic, potential, and total electronic energy for C–I covalent bond have been examined. It has been found that both delocalization indices of iodine covalent bond and the total electronic energy density integrated over carbon–iodine interatomic surface can be used as quantitative criteria of iodine-derived cation ability to form the halogen bond with triiodide anion in crystals.

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Acknowledgments

We thank Dr. P.A. Slepukhin for X-ray diffraction structural analysis of 1-iodomethyl-1,2-dihydro [1, 3] thiazolo[3,2-a]quinolinium monoiodide (CCDC 1055418) which was crystallized by E.A. Vershinina. This work was supported by the Russian Foundation for Basic Research, Grant 13-03-00767a and Grant 14-03-00961.

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Authors and Affiliations

  1. South Ural State University (National Research University), Lenin Prospect, 76, Chelyabinsk, Russia, 454080

    E. V. Bartashevich, S. E. Nasibullina & O. I. Bol’shakov

  2. D.I. Mendeleev University of Chemical Technology, Miusskaya Square 9, Moscow, Russia, 125047

    V. G. Tsirelson

Authors
  1. E. V. Bartashevich
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  2. S. E. Nasibullina
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  3. O. I. Bol’shakov
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  4. V. G. Tsirelson
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Correspondence to E. V. Bartashevich.

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This paper is dedicated to the memory of Professor Oleg Shishkin

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Bartashevich, E.V., Nasibullina, S.E., Bol’shakov, O.I. et al. Exploring heterocyclic cations ability to form the iodide–iodine halogen bond: case study of chalcogenazolo(ino)quinolinium crystals. Struct Chem 27, 305–313 (2016). https://doi.org/10.1007/s11224-015-0714-5

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  • DOI: https://doi.org/10.1007/s11224-015-0714-5

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