Premium
The planarity of heteroatom analogues of benzene: Energy component analysis and the planarization of hexasilabenzene
Author(s) -
Nakamura Taiji,
Kudo Takako
Publication year - 2019
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.25743
Subject(s) - planarity testing , heteroatom , chemical mechanical planarization , benzene , computational chemistry , silicon , chemistry , quantum chemical , molecule , crystallography , organic chemistry , layer (electronics) , ring (chemistry)
There are various nonplanar heteroatom analogues of benzene—cyclic 6π electron systems—and among them, hexasilabenzene (Si 6 H 6 ) is well known as a typical example. To determine the factors that control their planarity, quantum chemical calculations and an energy component analysis were performed. The results show that the energy components mainly controlling the planarity of benzene and hexasilabenzene are different. For hexasilabenzene, electron repulsion energy was found to be significantly important for the planarity. The application of the pseudo Jahn–Teller effect and the Carter–Goddard–Malrieu–Trinquier model for the interpretation of the planarity of the benzene analogues was also investigated. Furthermore, based on the quantitative results, it was revealed that the planarization of hexasilabenzene is realized by introducing substituents with π‐accepting ability, such as the boryl group, that bring about a reduction of the π‐electron repulsion on the silicon skeleton. © 2018 Wiley Periodicals, Inc.