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Computational ECD Spectrum Simulation of the Phytotoxin Scytalone: Importance of Solvent Effects on Conformer Populations
Author(s) -
Mazzeo Giuseppe,
Cimmino Alessio,
Andolfi Anna,
Evidente Antonio,
Superchi Stefano
Publication year - 2014
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22311
Subject(s) - conformational isomerism , polarizable continuum model , chemistry , time dependent density functional theory , computational chemistry , absolute configuration , molecular dynamics , density functional theory , solvent effects , solvation , circular dichroism , formalism (music) , chirality (physics) , molecule , chemical physics , stereochemistry , solvent , quantum mechanics , physics , organic chemistry , chiral symmetry , art , musical , nambu–jona lasinio model , visual arts , quark
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 1 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. Chirality 26:502–508, 2014 . © 2014 Wiley Periodicals, Inc.