Non-Classical Synthons: Supramolecular Recognition by S center dot center dot center dot O Chalcogen Bonding in Molecular Complexes of Riluzole

Thomas, Sajesh P and Kumar, Vijith and Alhameedi, Khidhir and Row, Guru TN (2019) Non-Classical Synthons: Supramolecular Recognition by S center dot center dot center dot O Chalcogen Bonding in Molecular Complexes of Riluzole. In: CHEMISTRY-A EUROPEAN JOURNAL, 25 (14). pp. 3591-3597.

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Abstract

Classical examples of supramolecular recognition units or synthons are the ones formed by hydrogen bonds. Here, we report the ubiquity of a S ... O chalcogen bonded synthon observed in a series of supramolecular complexes of the amyotrophic lateral sclerosis drug riluzole. Although the potential of higher chalcogens such as Se and Te to form robust and directional chalcogen bonded motifs is known, intermolecular sulfur chalcogen bonding is considered to be weak owing to the lower polarizability of S atoms. Here, the robustness and electronic nature of a S ... O chalcogen bonding non-classical synthon, and the origin of its exceptional directionality have been explored. Bond orders of the drug-coformer chalcogen bonding are found to be as high as one third of a single bond, and they are largely ionic in nature. The contribution of the S ... O chalcogen bonded motifs to the lattice energies of a series of crystals from the Cambridge Structural Database has been analyzed, showing they can be indeed significant, especially in molecules devoid of strong hydrogen bond donor groups.

Item Type:	Journal Article
Publication:	CHEMISTRY-A EUROPEAN JOURNAL
Publisher:	WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Additional Information:	Copyright belongs WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Keywords:	chalcogen bonding;crystal engineering;non-covalent interactions;supramolecular synthons
Department/Centre:	Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	23 Apr 2019 04:47
Last Modified:	23 Apr 2019 04:47
URI:	http://eprints.iisc.ac.in/id/eprint/62483

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