Influence of the CH/B replacement on the Reactivity of Boranthrene and Related Compounds.

Autor: Cortés I; Facultad de Ciencias Bioquímicas y Farmacéuticas, Instituto de Química Rosario (IQUIR, CONICET-UNR), Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Argentina., Cabrera-Trujillo JJ; Departamento de Química Orgánica I and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Faculdad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid (Spain)., Fernández I; Departamento de Química Orgánica I and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Faculdad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid (Spain).
Jazyk: angličtina
Zdroj: ACS organic & inorganic Au [ACS Org Inorg Au] 2021 Oct 06; Vol. 2 (1), pp. 44-52. Date of Electronic Publication: 2021 Oct 06 (Print Publication: 2022).
DOI: 10.1021/acsorginorgau.1c00023
Abstrakt: The influence of the replacement of CH groups by boron atoms on the reactivity of planar polycyclic aromatic hydrocarbons has been explored by means of computational tools. To this end, [4 + 2]-cycloaddition reactions involving anthracene and neutral boranthrene with different dienophiles such as ethylene, acetylene, and CO 2 have been compared. In addition, the influence of additional fused aromatic rings (pentacene or borapentacene) on the reactivity of these species has been also explored. It was found that the B-doped systems are systematically much more reactive than their all-carbon counterparts from both kinetic and thermodynamic points of view. The observed trends in reactivity are quantitatively analyzed in detail using state-of-the-art methods, namely, the activation strain model of reactivity and the energy decomposition analysis method. Our calculations reveal the importance of molecular orbital interactions as the key factor responsible for the enhanced reactivity of the B-doped systems.
Competing Interests: The authors declare no competing financial interest.
(© 2021 The Authors. Published by American Chemical Society.)
Databáze: MEDLINE
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