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.

中文翻译：

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苯衍生物的芳香性：剑桥结构数据库的探索。

分析了剑桥结构数据库（CSD）中最常见的固态苯环芳香性指数之一的芳香性谐波振荡器模型（HOMA）。苯，具有一个甲酰基，硝基，氨基或羟基的苯衍生物的HOMA直方图以及邻，间和对位的具有两个甲酰基，硝基，氨基或羟基的衍生物的直方图职位进行了调查。CSD中大多数取代苯衍生物的特征是HOMA值高，表明具有完全芳香性。但是，HOMA值从1到大约0的分布表明芳香性下降到非芳香性。在研究的苯衍生物中，芳香性的显着降低可能与间位带有二氨基和二硝基基团的化合物有关。