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Solution and Gas‐Phase Acidities of all‐trans (all‐E) Retinoic Acid: An Experimental and Computational Study |
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| Authors: | Prof Dr José‐Luis M Abboud Prof Dr Ilmar A Koppel Prof Dr Einar Uggerud Prof Dr Ivo Leito Dr Ivar Koppel Osamu Sekiguchi Dr Karl Kaupmees Jaan Saame Karl Kütt Prof Dr Masaaki Mishima |
| Institution: | 1. Institute for Materials Chemistry and Engineering, Kyushu University, 6‐10‐1, Hakozaki, Higashi‐ku, Fukuoka 812‐8581 (Japan), Fax: (+81)?92‐642‐2715;2. University of Tartu, Institute of Chemistry, Ravila 14a, 50411 Tartu (Estonia), Fax: (+372)?7‐375264;3. 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;4. Institute of Computer Sciences, University of Tartu, Liivi 2, 50409 Tartu (Estonia), Fax: (+372)?7‐375468 |
| 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. |
| Keywords: | acidity computational chemistry mass spectrometry retinoic acid UV/Vis spectrophotometry |