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Issue 4, 2015
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Introducing “carborazine” as a novel heterocyclic aromatic species

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Borazine is regarded as inorganic benzene, possessing a number of features analogous to aromatic benzene. The aromaticity of borazine, however, is a controversial matter to date. We propose a new heterocyclic species by introducing C, B and N atoms at opposite faces of a six-membered ring. This novel species, which we refer to as “carborazine,” possesses C2h symmetry, and more importantly it is aromatic. The aromaticity of carborazine is established by NICS values and supported by a number of topological parameters. Unlike borazine and benzene, carborazine possesses non-degenerate molecular orbitals and a relatively smaller HOMO–LUMO gap. Finally, we show the formation of phenol, aniline (by substitution) and naphthalene analogues (by fusion) of carborazine, which may suggest that a new class of heterocyclic species can be obtained using carborazine as building block.

Graphical abstract: Introducing “carborazine” as a novel heterocyclic aromatic species

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Article information

19 Nov 2014
17 Dec 2014
First published
08 Jan 2015

New J. Chem., 2015,39, 2483-2488
Article type

Introducing “carborazine” as a novel heterocyclic aromatic species

A. K. Srivastava and N. Misra, New J. Chem., 2015, 39, 2483
DOI: 10.1039/C4NJ02089H

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