Energetic effects of ether and ketone functional groups in 9,10-dihydroanthracene compound

Abstract

The energetic effects caused by replacing one of the methylene groups in the 9,10-dihydroanthracene by ether or ketone functional groups yielding xanthene and anthrone species, respectively, were determined from direct comparison of the standard (p degrees = 0 1 MPa) molar enthalpies of formation in the gaseous phase, at T = 298.15 K. of these compounds. The experimental static-bomb combustion calorimetry and Calvet microcalorimetry and the computational G3(MP2)//B3LYP method were used to get the standard molar gas-phase enthalpies of formation of xanthene. (41 8 +/- 3 5) kJ mol(-1), and anthrone, (31 4 +/- 3 2) kJ mol(-1) The enthalpic increments for the substitution of methylene by ether and ketone in the parent polycyclic compound (9,10-dihydroanthracene) are -(1179 +/- 5 5) kJ mol(-1) and -(1283 +/- 5.4) kJ mol(-1), respectively