2014/03/28 by Giuseppe Mazzeo, Alessio Cimmino, Anna Andolfi +2
Agricultural and Biological Sciences · Chemistry · #Analytical Chemistry and Chromatography #Molecular spectroscopy and chirality #Plant and animal studies
paper · doi:10.1002/chir.22311
openalex publication_date 2014/03/28 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29
A time-dependent Density Functional Theory (TDDFT) computational simulation of the electronic circular dichroism (ECD) spectrum of the phytotoxin scytalone (1), produced by different plant pathogenic fungi and involved in melanin production, was undertaken with the aim to establish a nonempirical correlation between the spectrum and the absolute configuration of this compound. In fact, very low optical rotation data of do not afford a reliable absolute configuration assignment while, on the contrary, the use of ECD can provide a useful tool for its stereochemical description. This structurally simple molecule displayed a considerable molecular flexibility, which made it mandatory to obtain an accurate conformers distribution to get a good reproduction of the experimental ECD spectrum. Only the application of an implicit integral equation formalism Polarizable Continuum Model (IEF-PCM) solvation model in the calculations allowed us to properly describe the conformer populations and finally obtain a more than satisfactory spectral simulation.