Impacts of external fields on aromaticity and acidity of benzoic acid: a density functional theory, conceptual density functional theory and information-theoretic approach study

• Published in: Physical chemistry chemical physics : PCCP 2023-01, Vol.25 (3), p.2595-265
• Main Authors: Li, Meng, Wan, Xinjie, He, Xin, Rong, Chunying, Liu, Shubin
• Format: Article
• Language: English
• Subjects: Aromaticity; Benzoic Acid; Density Functional Theory; Electric fields; Electricity; Information theory; Molecular Structure
• ISSN: 1463-9076; 1463-9084
• DOI: 10.1039/d2cp04557e

The impact of external fields on the molecular structure and reactivity properties has been of considerable interest in the recent literature. Benzoic acid as one of the most widely used compounds in medicinal and materials sciences is known for its dual propensity in aromaticity and acidity. In this work, we systematically investigate the impact of a uniform external electric field on these properties. We apply density functional theory, conceptual density functional theory, and an information-theoretic approach to appreciate the change pattern of aromaticity and acidity properties in external fields with different strengths. Our results show that they possess different change patterns under external fields, which can be satisfactorily rationalized by variations in reactivity descriptors and partial charges. The surprising yet novel results from this study should enrich the body of our knowledge about the impact of external fields for different kinds of electronic properties and provide guidance and foundation for future studies of this phenomenon in other molecular systems. Aromaticity and acidity propensities of benzoic acid are impacted differently by different strengths and directions of a uniform external field due to the different changing patterns in frontier orbitals and partial charges.