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A new type of C+⋯Hδ−(C=) bond in adducts of vinyl carbocations with alkenes Full article

Journal Scientific Reports
ISSN: 2045-2322
Output data Year: 2024, Volume: 14, Number: 1, Article number : 8818, Pages count : 8 DOI: 10.1038/s41598-024-58109-4
Authors Stoyanov Evgenii S. 1 , Bagryanskaya Irina Yu. 1 , Stoyanova Irina V. 1
Affiliations
1 Vorozhtsov Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

Abstract: By X-ray diffraction analysis and IR spectroscopy, it was established here that vinyl carbocations C3H5+/C4H7+ with carborane counterion CHB11Cl11− form stable monosolvates C3H5+⋅C3H6/C4H7+⋅C4H8 with molecules of alkenes C3H6/C4H8. They contain molecular group =C+⋯Hδ−–Cδ+= with a new type of bond formed by the H atom of the H–C= group of the alkene with the C atom of the C+=C group of the carbocation. The short C+----Cδ+ distance, equal to 2.44 Å, is typical of that of X----X in proton disolvates (L2H+) with an quasi-symmetrical X–H+⋯X moiety (where X = O or N) of basic molecule L. The nature of the discovered bond differs from that of the classic H–bond by an distribution of electron density: the electron–excessive Hδ− atom from the (=)C–H group of the alkene is attached to the C+ atom of the carbocation, on which the positive charge is predominantly concentrated. Therefore, it can be called an inverse hydrogen bond.
Cite: Stoyanov E.S. , Bagryanskaya I.Y. , Stoyanova I.V.
A new type of C+⋯Hδ−(C=) bond in adducts of vinyl carbocations with alkenes
Scientific Reports. 2024. V.14. N1. 8818 :1-8. DOI: 10.1038/s41598-024-58109-4 WOS Scopus OpenAlex
Dates:
Submitted: Dec 19, 2023
Accepted: Mar 25, 2024
Published online: Apr 10, 2024
Published print: Dec 1, 2024
Identifiers:
Web of science: WOS:001200298900023
Scopus: 2-s2.0-85189992855
OpenAlex: W4394693789
Citing: Пока нет цитирований
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