Preference in the Type of Halogen Bonding Interactions within Co-Crystals of Anthraquinone with a Pair of Isosteric Perhalobenzenes
Source abstract
Abstract
The preference in the type of halogen bond accepted by anthraquinone (C14H8O2) from two isosteric donors, namely 1,4-diiodoperfluorobenzene (C6I2F4) and 1,4-diiodoperchlorobenzene (C6I2Cl4), is reported. The two co-crystals, (C6I2F4)·(C14H8O2) and (C6I2Cl4)·(C14H8O2), are sustained primarily by I···O rather than π-type halogen bonds to form these multicomponent solids. The ability for each component to engage in two divergent halogen-bonding interactions generates a one-dimensional chain structure for each co-crystal. The bias in the halogen-bonding type is due to the difference in electrostatic potential between the carbonyl oxygen and the aromatic surface on the anthraquinone. To support this observed preference, the binding energies of the I···O halogen bond were quantified for both co-crystals by using density functional theory calculations and then compared to the interaction energy for related π-type halogen bond from previously reported structures.
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Research context
OpenAlex topics: Crystallography and molecular interactions · Chemical Thermodynamics and Molecular Structure · Crystallization and Solubility Studies
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Chemistry and Biochemistry, Missouri State University, Springfield, MO 65897, USA
Office of the Vice President for Research, University of Iowa, Iowa City, IA 52242, USA
Department of Natural Sciences and Mathematics, Webster University, St. Louis, MO 63119, USA
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