Energetic and Structural Studies of Two Biomass-Derived Compounds: 6-and 7-hydroxy-1-indanones

• Type: Article in International Scientific Journal
• Date: 2020

Authors

Ribeiro da Silva, ALR (Author) FCUP; Maria D M C R Ribeiro da Silva (Author) FCUP

Journal

Title: Applied Sciences

Vol. 10

Pages: 1-16

Publisher: MDPI

Indexing

ISI Web of Knowledge - 1 Citation

Scopus - 1 Citation

Other information

Authenticus ID: P-00T-243

DOI: 10.3390/app10238512

Abstract (EN): Featured Application This is a contribution for enlarging the thermodynamic database of organic compounds and ketone derivatives. These data are very relevant to controlling experimental investigations to produce value-added chemical products from biomass. Moreover, the knowledge from such data can be used in the development of schemes for the prediction of homologous properties of related compounds, in particular, modeling studies for the prediction of bio-oil composition. The energetic study of 6-hydroxy-1-indanone and 7-hydroxy-1-indanone was performed using experimental techniques and computational calculations. The enthalpies of combustion and sublimation of the two compounds were determined and allowed to derive the corresponding gas-phase standard molar enthalpies of formation. For this purpose, static-bomb combustion calorimetry and drop-method Calvet microcalorimetry were the experimental techniques used. Further, the enthalpy of fusion of each compound was obtained from scanning differential calorimetry measurements. Additionally, the gas-phase standard molar enthalpies of formation of these compounds were calculated through high-level ab initio calculations. The computational study of the molecular structures of the indanones was carried out and two possible conformers were observed for 6-hydroxy-1-indanone. Furthermore, the energetic effects associated with the presence of one hydroxyl group as a substituent on the benzenic ring of 1-indanone were also evaluated. Both experimental and theoretical methods show that 7-hydroxy-1-indanone is thermodynamically more stable than the 6-isomer in the gaseous phase and these results provide evidence for the existence of a strong intramolecular H-bond in 7-hydroxy-1-indanone. Finally, the intramolecular proton transfer in 7-hydroxy-1-indanone has been evaluated and as expected, it is not energetically favorable.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10