Aromaticity of benzene derivatives: an exploration of the Cambridge Structural Database. Issue 2 (6th April 2018)

• Record Type: Journal Article
• Authors: Majerz, Irena; Dziembowska, Teresa
• Is Part Of: Acta crystallographica. Volume 74:Issue 2(2018:Apr.)
• Page Start: 148
• Page End: 151
• Publication Date: 2018-04-06
• Subjects: HOMA -- Cambridge Structural Database -- benzene -- formyl groups -- nitro groups -- amino groups -- hydroxy groups -- aromaticity
• DOI: 10.1107/S2052520618000987
• Languages: English
• ISSNs: 2052-5206

Abstract

Abstract : The HOMA aromaticity index calculated for benzene derivatives in the Cambridge Structural Database shows stability in the benzene aromaticity but it is also possible to find many benzene compounds with significantly decreased aromaticity. Abstract : The harmonic oscillator model of aromaticity (HOMA) index, one of the most popular aromaticity indices for solid‐state benzene rings in the Cambridge Structural Database (CSD), has been analyzed. The histograms of HOMA for benzene, for benzene derivatives with one formyl, nitro, amino or hydroxy group as well as the histograms for the derivatives with two formyl, nitro, amino or hydroxy groups in ortho, meta and para positions were investigated. The majority of the substituted benzene derivatives in the CSD are characterized by a high value of HOMA, indicating fully aromatic character; however, the distribution of the HOMA value from 1 to about 0 indicates decreasing aromaticity down to non‐aromatic character. Among the benzene derivatives investigated, a significant decrease in aromaticity can be related to compounds with diamino and dinitro groups in the meta position.