Influence of Hydroxyl Functional Group on the Structure and Stability of Xanthone: A Computational Approach

• Published in: Molecules (Basel, Switzerland) Vol. 23; no. 11; p. 2962
• Main Authors: Freitas, Vera L S, Ribeiro da Silva, Maria D M C
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 13.11.2018; MDPI
• Subjects: Computer applications; conformers; Electrostatic properties; Energy; Equilibrium; Equilibrium analysis; Functional groups; gas-phase enthalpy of formation; Hydrocarbons; Hydrogen bonds; intramolecular hydrogen bond; Isomers; Molecular structure; monooxygenated xanthones; Potential energy; Structural stability; tautomers; thermodynamic properties; monooxygenated xanthones; tautomers; thermodynamic properties; conformers; gas-phase enthalpy of formation; intramolecular hydrogen bond
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules23112962

The present work addresses computational research focused on the energetic and structural properties of four isomers monohydroxyxanthone, using the G3(MP2)//B3LYP method, in order to evaluate the influence of the hydroxyl (-OH moiety) functional group on the xanthone molecule. The combination of these computational results with previous experimental data of these compounds enabled the determination of their enthalpies, entropies and Gibbs energies of formation, in the gaseous phase, and consequently to infer about the relative thermodynamic stability of the four isomers. Other issues were also addressed for the hydroxyxanthone isomers, namely the conformational and the tautomeric equilibrium analysis of the optimized molecular structures, the frontier orbitals, and the electrostatic potential energy maps. Complementarily, an energetic study of the intramolecular O - H ⋯ O hydrogen bond for 1-hydroxanthone was also performed.