Issue 39, 2021

Participation of S and Se in hydrogen and chalcogen bonds

Abstract

This article reviews the history and the current state of knowledge concerning the ability of the heavy chalcogen atoms S and Se, and to some extent Te, to participate in a H-bond as either proton donor or acceptor. These atoms are nearly as effective proton acceptors as O, and only slightly weaker as donor. They can also participate in chalcogen bonds where they act as electron acceptors from a nucleophile. These bonds rapidly strengthen as the chalcogen atom becomes larger: S < Se < Te, or if they are surrounded by electron-withdrawing substituents, and can exceed that of many types of H-bonds. Experimental and computational evidence indicates that both H-bonds and chalcogen bonds involving S and Se occur widely in chemical and biological systems, and play an active role in structure and function.

Graphical abstract: Participation of S and Se in hydrogen and chalcogen bonds

Article information

Article type
Highlight
Submitted
08 Aug. 2021
Accepted
08 Sept. 2021
First published
08 Sept. 2021

CrystEngComm, 2021,23, 6821-6837

Author version available

Participation of S and Se in hydrogen and chalcogen bonds

S. Scheiner, CrystEngComm, 2021, 23, 6821 DOI: 10.1039/D1CE01046H

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