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Solution and Gas‐Phase Acidities of all‐trans ( all‐E ) Retinoic Acid: An Experimental and Computational Study
Author(s) -
Abboud JoséLuis M.,
Koppel Ilmar A.,
Uggerud Einar,
Leito Ivo,
Koppel Ivar,
Sekiguchi Osamu,
Kaupmees Karl,
Saame Jaan,
Kütt Karl,
Mishima Masaaki
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500717
Subject(s) - retinoic acid , gas phase , chemistry , phase (matter) , thermodynamics , physics , organic chemistry , biochemistry , gene
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.