Benzothienoiodolium Cations Doubly Bonded to Anions via Halogen-Chalcogen and Halogen-Hydrogen Supramolecular Synthons

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F23%3A43934002" target="_blank" >RIV/60461373:22310/23:43934002 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1021/acs.cgd.2c01485" target="_blank" >https://doi.org/10.1021/acs.cgd.2c01485</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.cgd.2c01485" target="_blank" >10.1021/acs.cgd.2c01485</a>

Result language
angličtina
Original language name
Benzothienoiodolium Cations Doubly Bonded to Anions via Halogen-Chalcogen and Halogen-Hydrogen Supramolecular Synthons
Original language description
The simultaneous binding of a molecular entity through two interactions is a frequently pursued recognition mode due to the advantages it offers in securing molecular self-assembly. Here, we report how the planarity of the benzothienoiodolium (BTI) cation allows for preorganizing in the cation plane the hydrogen, halogen, and chalcogen bonds (HBs, XBs, and ChBs, respectively) formed by the phenyl hydrogen, iodolium iodine, and thienyl sulfur. Crystallographic analyses of some BTI salts show how this interaction coplanarity enables their coupling to point toward a single anion that is coordinated via the supramolecular and heteroditopic synthon XB/HB or XB/ChB, the latter observed here for the first time. These synthons adopt a Janus-like arrangement around iodine. Crystallographic information suggests that interactions of the synthons act synergistically, e.g., when resulting in the unusually short ChBs formed by the thienyl sulfur. Determination of the molecular electrostatic potential, Bader’s quantum theory of “atoms-in-molecules” analysis, and natural bond orbital investigations give information on the nature and energetic aspects of the short contacts observed in crystals. © 2023 American Chemical Society.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10400 - Chemical sciences

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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