Embedding a Planar Hypercoordinate Carbon Atom into a [4n+2] π‐System

• Published in: Chemphyschem Vol. 21; no. 2; pp. 145 - 148
• Main Authors: Yañez, Osvaldo, Báez‐Grez, Rodrigo, Garza, Jorge, Pan, Sudip, Barroso, Jorge, Vásquez‐Espinal, Alejandro, Merino, Gabriel, Tiznado, William
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 16.01.2020
• Subjects: Aromatic hydrocarbons; Aromaticity; bonding analysis; Carbon; Electronegativity; Electronic properties; Electronic structure; Embedded systems; Embedding; Hydrocarbons; Hydrogen atoms; induced magnetic field; planar hypercoordinate carbon; theoretical chemistry; theoretical chemistry; Aromaticity; bonding analysis; planar hypercoordinate carbon; induced magnetic field
• ISSN: 1439-4235; 1439-7641
• DOI: 10.1002/cphc.201900998

Through delicate tuning of the electronic structure, we report herein a rational design of seventeen new putative global minimum energy structures containing a planar tetra‐ or pentacoordinate carbon atom embedded in an aromatic hydrocarbon. These structures are the result of replacing three consecutive hydrogen atoms of an aromatic hydrocarbon by less electronegative groups, forming a multicenter σ‐bond with the planar hypercoordinate carbon atom and participating in the π‐electron delocalization. This strategy that maximizes both mechanical and electronic effects through aromatic architectures can be extended to several molecular combinations to achieve new and diverse compounds containing planar hypercoordinate carbon centers. Planar hypercoordinate carbon compounds: Calculations demonstrate that by replacing three consecutive hydrogens in an aromatic hydrocarbon with less electronegative groups, it is possible to obtain viable structures (putative global minima) with a planar hypercoordinate carbon (tetra‐ and pentacoordinate).