Phenylnaphthalenes: sublimation equilibrium, conjugation, and aromatic interactions

The Journal of Physical Chemistry. B
Carlos F R A C LimaLuís M N B F Santos

Abstract

In this work, the interplay between structure and energetics in some representative phenylnaphthalenes is discussed from an experimental and theoretical perspective. For the compounds studied, the standard molar enthalpies, entropies and Gibbs energies of sublimation, at T = 298.15 K, were determined by the measurement of the vapor pressures as a function of T, using a Knudsen/quartz crystal effusion apparatus. The standard molar enthalpies of formation in the crystalline state were determined by static bomb combustion calorimetry. From these results, the standard molar enthalpies of formation in the gaseous phase were derived and, altogether with computational chemistry at the B3LYP/6-311++G(d,p) and MP2/cc-pVDZ levels of theory, used to deduce the relative molecular stabilities in various phenylnaphthalenes. X-ray crystallographic structures were obtained for some selected compounds in order to provide structural insights, and relate them to energetics. The thermodynamic quantities for sublimation suggest that molecular symmetry and torsional freedom are major factors affecting entropic differentiation in these molecules, and that cohesive forces are significantly influenced by molecular surface area. The global results obtai...Continue Reading

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Citations

Feb 13, 2014·The Journal of Physical Chemistry. a·Inês M RochaManuel A V Ribeiro da Silva
Nov 3, 2016·Journal of Chemical Information and Modeling·James L McDonaghJohn B O Mitchell
Mar 2, 2017·The Journal of Organic Chemistry·Chieh-Kai ChanMeng-Yang Chang
Mar 8, 2017·The Journal of Physical Chemistry. a·Carlos F R A C LimaLuís M N B F Santos
Jun 26, 2012·Chemistry : a European Journal·Carlos F R A C LimaLuís M N B F Santos
Jul 14, 2018·Acta Crystallographica. Section E, Crystallographic Communications·U Mohamooda SumayaG Usha

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