Energetically More Stable Singlet Cyclopentane-1,3-diyl Diradical with π-Single Bonding Character than the Corresponding σ-Single Bonded Compound

Liu Qian

Onishi Keita

Miyazawa Yuki

Wang Zhe

Hatano Sayaka

Abe Manabu

Journal of the American Chemical Society

Carbon–carbon σ-single bonds are crucial for constructing molecules like ethane derivatives (R3C–CR3), which are composed of tetrahedral four-coordinate carbons. Molecular functions, such as light absorption or emission, originate from the π-bonds existing in ethylene derivatives (R2C═CR2). In this study, a relatively stable cyclopentane-1,3-diyl species with π-single bonding system (C−π–C) with planar four-coordinate carbons is constructed. This diradicaloid is energetically more stable than the corresponding σ-single bonding system. The π-electron single bonding system provides deeper insights into the chemical bonding and the physical properties derived from the small energy gaps between the bonding and antibonding molecular orbitals.

eng

American Chemical Society

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.3c10971

This is not the published version. Please cite only the published version.

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[DOI] https://doi.org/10.1021/jacs.3c10971 isVersionOf

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