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

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

Журнал

Scientific Reports
ISSN: 2045-2322

Вых. Данные

Год: 2024, Том: 14, Номер: 1, Номер статьи : 8818, Страниц : 8 DOI: 10.1038/s41598-024-58109-4

Авторы

Stoyanov Evgenii S. ¹ , Bagryanskaya Irina Yu. ¹ , Stoyanova Irina V. ¹

Организации

1	Vorozhtsov Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

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.

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

Поступила в редакцию:	19 дек. 2023 г.
Принята к публикации:	25 мар. 2024 г.
Опубликована online:	10 апр. 2024 г.
Опубликована в печати:	1 дек. 2024 г.

Web of science:	WOS:001200298900023
Scopus:	2-s2.0-85189992855
OpenAlex:	W4394693789

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