title: Computational ECD spectrum simulation of the phytotoxin scytalone: importance of solvent effects on conformer populations.
abstract: 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.
authors.affiliation: Dipartimento di Scienze, Università della Basilicata, Potenza, Italy.
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Mazzeo
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
authors.forename: Stefano
authors.initials: S
authors.lastname: Superchi
keywords: TDDFT CD calculations; absolute configuration; conformations; electronic circular dichroism; melanin; naphthalenones