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The nature of [N–Cl–N]+ and [N–F–N]+ halogen bonds in solution
(organisk kemi)ORCID iD: 0000-0003-0359-5970
2014 (English)In: Chemical Science, Vol. 5, p. 3226-3233Article in journal (Refereed) Published
Abstract [en]

Halonium ions are synthetically useful, transient species that may be stabilized by attachment to two electron donors. Whereas studies of [C–X–C]+-type ions have greatly contributed to the fundamental understanding of chemical bonding and reaction mechanisms, investigations of the corresponding [N–X–N]+ halogen bond complexes are only at an early stage. Herein we present solution NMR spectroscopic and theoretical evidence for the nature of [N–Cl–N]+ and [N–F–N]+ complexes, and we discuss their geometries and stabilities in comparison to their iodine and bromine-centered analogues as well as the corresponding three-center [N–H–N]+ hydrogen bond. We show the chlorine-centered halogen bond to be weaker but yet to resemble the symmetric geometry of the three-center bond of heavier halogens. In contrast, the [N–F–N]+ bond is demonstrated to prefer asymmetric geometry analogous to the [N–H–N]+ hydrogen bond. However, the [N–F–N]+ system has a high energy barrier for interconversion, and due to entropy loss, its formation is slightly endothermic.

Place, publisher, year, edition, pages
2014. Vol. 5, p. 3226-3233
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-356021OAI: oai:DiVA.org:uu-356021DiVA, id: diva2:1232435
Available from: 2018-07-11 Created: 2018-07-11 Last updated: 2018-07-11

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Erdelyi, Mate
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