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Theoretical studies and vibrational spectra of 1H-indole-3-acetic acid. Exploratory conformational analysis of dimeric species

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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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Acknowledgments

Thanks are due to Agencia de Promoción Científica y Tecnológica Argentina (MINCYT), CONICET and Universidad Nacional de La Plata (Argentina) for financial support. A.H.J. is Member of the Scientific Research Career (CIC, Provincia de Buenos Aires). A.A.V. is a Research Member of the National Research Council of Argentina (CONICET). M.C.P.S. acknowledges a fellowship (IP-PRH N0 54) from Agencia de Promoción Científica y Tecnológica Argentina and Universidad de la Cuenca del Plata (Corrientes, Argentina) and R.M.L. acknowledges Universidad de la Cuenca del Plata for facilities provided during the course of this work.

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Authors and Affiliations

  1. Facultad de Ingeniería, Universidad de la Cuenca del Plata, Lavalle 50, 3400, Corrientes, Argentina

    Rosana Maria Lobayan & María Celia Pérez Schmit

  2. CEQUINOR Facultad de Ciencias Exactas y Facultad de Ingeniería, Universidad Nacional de La Plata, CC 962, 1900, La Plata, Argentina

    Alicia H. Jubert

  3. PRALIB (UBA, CONICET), Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, C1113AAD, Buenos Aires, Argentina

    Arturo Vitale

Authors
  1. Rosana Maria Lobayan
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  2. María Celia Pérez Schmit
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  3. Alicia H. Jubert
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  4. Arturo Vitale
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Corresponding author

Correspondence to Rosana Maria Lobayan.

Additional information

Rosana Maria Lobayan and María Celia Pérez Schmit contributed equally to this work

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Lobayan, R.M., Pérez Schmit, M.C., Jubert, A.H. et al. Theoretical studies and vibrational spectra of 1H-indole-3-acetic acid. Exploratory conformational analysis of dimeric species. J Mol Model 17, 1381–1392 (2011). https://doi.org/10.1007/s00894-010-0833-2

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