Show simple item record

dc.contributor.authorAms, Mark R.
dc.contributor.authorTrapp, Nils
dc.contributor.authorSchwab, Anatol
dc.contributor.authorMilić, Jovana V.
dc.contributor.authorDiederich, François
dc.date.accessioned2019-03-11T17:57:25Z
dc.date.available2019-03-11T17:57:25Z
dc.date.issued2018-12-11
dc.identifier.citationAms, M. R., Trapp, N., Schwab, A., Milić, J. V., & Diederich, F. (2019). Chalcogen bonding “2S–2N squares” versus competing interactions: Exploring the recognition properties of sulfur. Chemistry – A European Journal, 25(1), 323-333. doi:10.1002/chem.201804261en_US
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.urihttp://hdl.handle.net/10456/48126
dc.description.abstract" Chalcogen bonding (CB) is the focus of increased attention for its applications in medicinal chemistry, materials science, and crystal engineering. However, the origin of sulfur's recognition properties remains controversial, and experimental evidence for supporting theories is still emerging. Here, a comprehensive evaluation of sulfur CB interactions is presented by investigating 2,1,3‐benzothiadiazole X‐ray crystallographic structures gathered from the Cambridge Structure Database (CSD), Protein Data Bank (PDB), and own laboratory findings. Through the systematic analysis of substituent effects on a subset library of over thirty benzothiadiazole derivatives, the competing interactions have been categorized into four main classes, namely 2S–2N CB square, halogen bonding (XB), S⋅⋅⋅S, and hydrogen‐bonding (HB). A geometric model is employed to characterize the 2S–2N CB square motifs and discuss the role of electrostatic, dipole, and orbital contributions toward the interaction."en_US
dc.description.sponsorshipThis work was supported by a grant from the Swiss National Science Foundation SNF 200020_159802. M.R.A. gratefully acknowledges the opportunity and financial support from ETH Zürich as a guest professor in the laboratory of Prof. Dr. François Diederich in 2016, and Allegheny College for financial support.en_US
dc.language.isoen_USen_US
dc.publisherWileyen_US
dc.relation.ispartofChemistry - A European Journalen_US
dc.relation.isversionofhttps://onlinelibrary.wiley.com/doi/full/10.1002/chem.201804261en_US
dc.rightsThis is the peer reviewed version of the following article: Ams, M. R., Trapp, N., Schwab, A., Milić, J. V., & Diederich, F. (2019). Chalcogen bonding “2S–2N squares” versus competing interactions: Exploring the recognition properties of sulfur. Chemistry – A European Journal, 25(1), 323-333. doi:10.1002/chem.201804261, which has been published in final form at https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201804261. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.en_US
dc.subject2,1,3-benzothiadiazoleen_US
dc.subject2S–2N squareen_US
dc.subjectchalcogen bondingen_US
dc.subjectsulfuren_US
dc.subjectX-ray crystallographyen_US
dc.titleChalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfuren_US
dc.description.versionPublished articleen_US
dc.contributor.departmentChemistryen_US
dc.description.embargoThis version of the article is available for viewing to the public after December 11, 2019en_US
dc.citation.volume25en_US
dc.citation.issue1en_US
dc.citation.spage223en_US
dc.citation.epage233en_US
dc.identifier.doi10.1002/chem.201804261
dc.contributor.avlauthorAms, Mark R.


Files in this item

Thumbnail
Thumbnail

This item appears in the following Collection(s)

Show simple item record