Theoretical studies and vibrational spectra of <Emphasis Type="Italic">1H</Emphasis>-indole-3-acetic acid. Exploratory conformational analysis of dimeric species |
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Authors: | Rosana Maria Lobayan María Celia Pérez Schmit Alicia H Jubert Arturo Vitale |
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Institution: | 1.Facultad de Ingeniería,Universidad de la Cuenca del Plata,Corrientes,Argentina;2.CEQUINOR Facultad de Ciencias Exactas y Facultad de Ingeniería,Universidad Nacional de La Plata,La Plata,Argentina;3.PRALIB (UBA, CONICET), Facultad de Farmacia y Bioquímica,Universidad de Buenos Aires,Buenos Aires,Argentina |
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Abstract: | Theoretical studies on 1H-indole-3-acetic acid (IAA) were performed to investigate the conformational properties of dimeric species and vibrational
spectra. Experimental infrared spectra at 100 K and 297 K and Raman spectrum at 297 K were analyzed and compared against calculations
performed at B3LYP/6-31G** level. A exploratory study of the conformational space of dimeric species was performed. Our analysis
showed that dimeric forms predicted theoretically contribute distinctively to the assignments of experimental results. These
structures are defined by the orientation of the acetyl moieties with respect to the plane of indole ring. The dimers are
formed by two symmetrical IAA monomers (one of them with the acetyl moiety upward oriented, Re-face, and the other isomer having the acetyl moiety downward oriented, Si-face) in tail-to-tail way. The X-ray geometry and FTIR vibrational frequencies were compared with the results of DFT calculations.
A conformational equilibrium involving the non-equivalent IAA dimers: CCT-CCT, A+A+T-A-A-T, A+A-T-A-A+T, and A+CT-A-CT was found. The relation of the conformational properties of the IAA molecule with the features of the vibrational spectra
was described in detail. The band assignments were discussed as related to the conformations properties. Our analysis shows
the significance of the theoretical study of the conformational space of the monomeric molecule in the rationalization of
experimental results. |
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