Participation of S and Se in hydrogen and chalcogen bonds

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...

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Bibliographic Details
Published inCrystEngComm Vol. 23; no. 39; pp. 6821 - 6837
Main Author Scheiner, Steve
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 11.10.2021
Subjects
Bonding strength
Chalcogen bonds
Nucleophiles
Protons
Tellurium
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Summary: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. The heavier chalcogen atoms S, Se, and Te can each participate in a range of different noncovalent interactions. They can serve as both proton donor and acceptor in H-bonds. Each atom can also act as electron acceptor in a chalcogen bond.
Bibliography:After attaining his BS degree in chemistry at City College of New York in 1972, Steve Scheiner conducted molecular orbital studies of enzyme activity under the supervision of William N. Lipscomb at Harvard University, completing his PhD in 1976. Following a two-year Weizmann Postdoctoral Fellowship at Ohio State University, he began his independent career on the faculty of Southern Illinois University, where his research focused on H-bonds and the proton transfers that occur within, in both the ground and excited states. In 2000, he moved to his current position at Utah State University, where his interests broadened into noncovalent bonds in a more general sense, including the full spectrum of halogen, chalcogen, pnicogen, tetrel, triel, and aerogen bonds.
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ISSN:1466-8033
1466-8033
DOI:10.1039/d1ce01046h