Abstract
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.
Highlights
Accurate data about thermochemical and thermophysical properties of biomass-derived compounds are essential for the evaluation of the corresponding chemical behavior
Our research group has been involved in an extensive experimental and theoretical thermodynamic study on key biomass-derived compounds, namely, vanillyl alcohol [1], levoglucosan [4], cellulose allomorphs [5], α-D-xylose [6], and more recently, cyclopentenones [7], indanones [2], and other classes of relevant compounds extracted from biomass
In energetic effects associated with the presence of a hydroxyl group on the core of the benzenic ring of addition, addition, we we addressed addressed the the energetic energetic effects effects associated associated with with the the presence presence of of aa hydroxyl hydroxyl group group on on the the
Summary
Accurate data about thermochemical and thermophysical properties of biomass-derived compounds are essential for the evaluation of the corresponding chemical behavior These data are very relevant when controlling experimental investigations to produce value-added chemical products from biomass. Data can be used in the development of schemes for the prediction of the homologous properties of related compounds [1,2], in particular, modeling studies for the prediction of bio-oil composition [3] In this context, our research group has been involved in an extensive experimental and theoretical thermodynamic study on key biomass-derived compounds, namely, vanillyl alcohol [1], levoglucosan [4], cellulose allomorphs [5], α-D-xylose [6], and more recently, cyclopentenones [7], indanones [2], and other classes of relevant compounds extracted from biomass.
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