title: Solution and gas-phase acidities of all-trans (all-E) retinoic acid: an experimental and computational study.
abstract: Retinoic acid is of fundamental biological importance. Its acidity was determined in the gas phase and in acetonitrile solution by means of mass spectrometry and UV/Vis spectrophotometry, respectively. The intrinsic acidity is slightly higher than that of benzoic acid. In solution, the situation is opposite. The experimental systems were described theoretically applying quantum chemical methods (wave function theory and density functional theory). This allowed the determination of the molecular structure of the acid and its conjugate base, both in vacuo and in solution, and for computational estimates of its acidity in both phases.
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan), Fax: (+81) 92-642-2715. abboud@ms.ifoc.kyushu-u.ac.jp.
authors.forename: José-Luis M
authors.initials: JL
authors.lastname: Abboud
authors.affiliation: University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu (Estonia), Fax: (+372) 7-375264. ilmar@chem.ut.ee.
authors.forename: Ilmar A
authors.initials: IA
authors.lastname: Koppel
authors.affiliation: Mass Spectrometric Laboratory and Center for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, University of Oslo, P.O.B. 1033, Blindern, 0315 Oslo (Norway), Fax: (+47) 22855441. einar.uggerud@kjemi.uio.no.
authors.forename: Einar
authors.initials: E
authors.lastname: Uggerud
authors.affiliation: University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu (Estonia), Fax: (+372) 7-375264. ivo.leito@ut.ee.
authors.forename: Ivo
authors.initials: I
authors.lastname: Leito
authors.affiliation: Institute of Computer Sciences, University of Tartu, Liivi 2, 50409 Tartu (Estonia), Fax: (+372) 7-375468. Ivar.Koppel@ut.ee.
authors.forename: Ivar
authors.initials: I
authors.lastname: Koppel
authors.affiliation: Mass Spectrometric Laboratory and Center for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, University of Oslo, P.O.B. 1033, Blindern, 0315 Oslo (Norway), Fax: (+47) 22855441.
authors.forename: Osamu
authors.initials: O
authors.lastname: Sekiguchi
authors.affiliation: University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu (Estonia), Fax: (+372) 7-375264.
authors.forename: Karl
authors.initials: K
authors.lastname: Kaupmees
authors.affiliation: University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu (Estonia), Fax: (+372) 7-375264.
authors.forename: Jaan
authors.initials: J
authors.lastname: Saame
authors.affiliation: University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu (Estonia), Fax: (+372) 7-375264.
authors.forename: Karl
authors.initials: K
authors.lastname: Kütt
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan), Fax: (+81) 92-642-2715. mishima@ms.ifoc.kyushu-u.ac.jp.
authors.forename: Masaaki
authors.initials: M
authors.lastname: Mishima
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D000143:Acids / Q000737:chemistry; D005740:Gases / Q000737:chemistry; D008958:Models, Molecular; D011789:Quantum Theory; D012996:Solutions; D013816:Thermodynamics; D014212:Tretinoin / Q000737:chemistry*
chemical_list: D000097:Acetonitriles; D000143:Acids; D005740:Gases; D012996:Solutions; D014212:Tretinoin; C032159:acetonitrile
keywords: UV/Vis spectrophotometry; acidity; computational chemistry; mass spectrometry; retinoic acid