π Aromaticity and Three-Dimensional Aromaticity: Two sides of the Same Coin?

J. Poater, M. Sola, C. Vinas, F. Teixidor

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

A bridge between classical organic polycyclic aromatic hydrocarbons (PAH) and closo borohydride clusters is established by showing that they share a common origin regulated by the number of valence electrons in an electronic confined space. Application of the proposed electronic confined space analogy (ECSA) method to archetypal PAHs leads to the conclusion that the 4n+2 Wade-Mingos rule for three-dimensional closo boranes is equivalent to the (4n+2)π Hückel rule for two-dimensional PAHs. More importantly, use of ECSA allows design of new interesting fused closo boranes which can be a source of inspiration for synthetic chemists.
Original languageEnglish
Pages (from-to)12191-12195
JournalAngewandte Chemie International Edition in English
Issue number53
DOIs
Publication statusPublished - 2014

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