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Article

The Balance between Hydrogen Bonds, Halogen Bonds, and Chalcogen Bonds in the Crystal Structures of a Series of 1,3,4-Chalcogenadiazoles

by
Viraj De Silva
,
Boris B. Averkiev
,
Abhijeet S. Sinha
and
Christer B. Aakeröy
*
Department of Chemistry, Kansas State University, Manhattan, KS 66506, USA
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(14), 4125; https://doi.org/10.3390/molecules26144125
Submission received: 22 May 2021 / Revised: 2 July 2021 / Accepted: 5 July 2021 / Published: 7 July 2021
(This article belongs to the Special Issue Structural Changes in Supramolecular Complexes)
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Abstract

In order to explore how specific atom-to-atom replacements change the electrostatic potentials on 1,3,4-chalcogenadiazole derivatives, and to deliberately alter the balance between intermolecular interactions, four target molecules were synthesized and characterized. DFT calculations indicated that the atom-to-atom substitution of Br with I, and S with Se enhanced the σ-hole potentials, thus increasing the structure directing ability of halogen bonds and chalcogen bonds as compared to intermolecular hydrogen bonding. The delicate balance between these intermolecular forces was further underlined by the formation of two polymorphs of 5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine; Form I displayed all three interactions while Form II only showed hydrogen and chalcogen bonding. The results emphasize that the deliberate alterations of the electrostatic potential on polarizable atoms can cause specific and deliberate changes to the main synthons and subsequent assemblies in the structures of this family of compounds.
Keywords: chalcogen bond; halogen bond; hydrogen bond; intermolecular interactions; polymorphism; σ-hole chalcogen bond; halogen bond; hydrogen bond; intermolecular interactions; polymorphism; σ-hole

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MDPI and ACS Style

De Silva, V.; Averkiev, B.B.; Sinha, A.S.; Aakeröy, C.B. The Balance between Hydrogen Bonds, Halogen Bonds, and Chalcogen Bonds in the Crystal Structures of a Series of 1,3,4-Chalcogenadiazoles. Molecules 2021, 26, 4125. https://doi.org/10.3390/molecules26144125

AMA Style

De Silva V, Averkiev BB, Sinha AS, Aakeröy CB. The Balance between Hydrogen Bonds, Halogen Bonds, and Chalcogen Bonds in the Crystal Structures of a Series of 1,3,4-Chalcogenadiazoles. Molecules. 2021; 26(14):4125. https://doi.org/10.3390/molecules26144125

Chicago/Turabian Style

De Silva, Viraj, Boris B. Averkiev, Abhijeet S. Sinha, and Christer B. Aakeröy. 2021. "The Balance between Hydrogen Bonds, Halogen Bonds, and Chalcogen Bonds in the Crystal Structures of a Series of 1,3,4-Chalcogenadiazoles" Molecules 26, no. 14: 4125. https://doi.org/10.3390/molecules26144125

APA Style

De Silva, V., Averkiev, B. B., Sinha, A. S., & Aakeröy, C. B. (2021). The Balance between Hydrogen Bonds, Halogen Bonds, and Chalcogen Bonds in the Crystal Structures of a Series of 1,3,4-Chalcogenadiazoles. Molecules, 26(14), 4125. https://doi.org/10.3390/molecules26144125

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