Neutral, ion gas-phase energetics and structural properties of hydroxybenzophenones
Juan Z Dávalos1, Andrés Guerrero, Rebeca Herrero
1Instituto de Quimica-Fisica Rocasolano, CSIC, Serrano 119, 28006, Madrid, Spain. jdavalos@iqfr.csic.es
Abstract:
We have carried out a study of the energetics, structural, and physical properties of o-, m-, and p-hydroxybenzophenone neutral molecules, C(13)H(10)O(2), and their corresponding anions. In particular, the standard enthalpies of formation in the gas phase at 298.15 K for all of these species were determined. A reliable experimental estimation of the enthalpy associated with intramolecular hydrogen bonding in chelated species was experimentally obtained. The gas-phase acidities (GA) of benzophenones, substituted phenols, and several aliphatic alcohols are compared with the corresponding aqueous acidities (pK(a)), covering a range of 278 kJ.mol(-1) in GA and 11.4 in pK(a). A computational study of the various species shed light on structural effects and further confirmed the self-consistency of the experimental results.
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