Experimental isolation and spectroscopic characterization of squamocin acetogenin combining FT-IR, FT-Raman and UV–Vis spectra with DFT calculations

Squamocin, an annonaceous acetogenin has been experimentally isolated and characterized in the solid state using the FT-IR and FT-Raman spectra and in methanol solution by UV–visible spectrum. The main bands observed were assigned combining the IR and Raman spectra with hybrid functional B3LYP/6-31G...

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Bibliographic Details
Published in:Journal of molecular structure 2020-11, Vol.1219, p.128610-128610, Article 128610
Main Authors: Hidalgo, José Ruiz, Neske, Adriana, Iramain, Maximiliano A., Alvarez, Patricia E., Bongiorno, Patricio Leyton, Brandán, Silvia Antonia
Format: Article
Language:English
Subjects:
Acetogenin
DFT calculations
Molecular structure
Squamocin
Vibrational spectra
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Summary:Squamocin, an annonaceous acetogenin has been experimentally isolated and characterized in the solid state using the FT-IR and FT-Raman spectra and in methanol solution by UV–visible spectrum. The main bands observed were assigned combining the IR and Raman spectra with hybrid functional B3LYP/6-31G∗ calculations. Structural, electronic and topological properties were predicted at the same level of theory for the most stable conformer of squamocin in gas phase and methanol solution. A corrected solvation energy value of −147.54 kJ/mol was predicted for squamocin in methanol while the atomic population natural (NPA) charges evidence higher values on O atoms of R2 and R3 rings, as compared with the corresponding to lactone ring. Mapped MEP surfaces suggest that nucleophilic regions are located on the O atoms of three rings and of OH bonds belonging to side chain, in agreement with the higher charges values evidenced on these O atoms while electrophilic regions are predicted on the H atoms of OH groups. High stabilities of squamocin in both media was revealed by AIM studies while only in methanol solution by NBO calculations. The expansion of volume and the higher dipole moment in methanol suggest a clear solvation of squamocin by solvent molecules. Gap values have evidenced that squamocin is most reactive in methanol while that its large aliphatic chain produces an increases the reactivity of this γ-lactone, as compared with ascorbic acid lactone. Reasonable concordances among the predicted UV–visible and IR, Raman spectra with the corresponding experimental ones were found. [Display omitted] •Squamocin acetogenin has been isolated and characterized by IR and Raman spectra.•Structural properties were studied by hybrid functional B3LYP/6-31G∗ calculations.•Corrected solvation energy of −147.54 kJ/mol was predicted for squamocin in methanol.•Nucleophilic regions located on the O atoms of three rings were found.•High stabilities of squamocin in both media was revealed by AIM studies.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2020.128610