An experimental and density functional study on conformational and spectroscopic analysis of 5-methoxyindole-2-carboxylic acid

•Vibrational spectra were examined via FT-IR, FT-Raman and DFT calculations.•Electronic transitions were investigated in solution environment.•Magnetic features were determined depending on predicted and recorded NMR spectra.

In this article, a brief conformational and spectroscopic characterization of 5-methoxyindole-2-carboxylic acid (5-MeOICA) via experimental techniques and applications of quantum chemical methods is presented. The conformational analysis of the studied molecule was determined theoretically using density functional computations for ground state, and compared with previously reported experimental findings. The vibrational transitions were examined by measured FT-IR and FT-Raman spectroscopic data, and also results obtained from B3LYP and CAM-B3LYP functionals in combination with 6-311++G(d,p) basis set. The recorded proton and carbon NMR spectra in DMSO solution were analyzed to obtain the exact conformation. Due to intermolecular hydrogen bondings, NMR calculations were performed for the dimeric form of 5-MeOICA and so chemical shifts of those protons were predicted more accurately. Finally, electronic properties of steady compound were identified by a comparative study of UV absorption spectra in ethanol and water solution and TD-DFT calculations.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide