Neutral, Ion Gas-Phase Energetics and Structural Properties of Hydroxybenzophenones

• Type: Article in International Scientific Journal
• Date: 2010

Authors

Juan Z Davalos (Author) Other; Andres Guerrero (Author) Other; Rebeca Herrero (Author) Other; Pilar Jimenez (Author) Other; Antonio Chana (Author) Other; Jose Luis M Abboud (Author) Other; Carlos F R A C Lima (Author) Other; Luis M N B F Santos (Author) FCUP; Alexsandre F Lago (Author) Other

Journal

Title: Journal of Organic Chemistry

Vol. 75 No. 8

Pages: 2564-2571

ISSN: 0022-3263

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 18 Citations

Scopus - 18 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-003-7F6

DOI: 10.1021/jo100085b

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8