title: Multitechnique investigation of conformational features of small molecules: the case of methyl phenyl sulfoxide.
abstract: The conformational distribution of methyl phenyl sulfoxide (a molecule representative of a very important class of reagents widely used in asymmetric synthesis) has been studied in two different phases of matter (gas phase and solution) by a comprehensive approach including theoretical calculations, microwave spectroscopy, liquid crystal NMR experiments, and atomistic molecular dynamics computer simulations. The aim was to investigate the combined action of intra- and intermolecular interactions in determining the molecule's conformational equilibrium, upon which important physicochemical properties (inter alia, the chemoselectivity) significantly depend. Basically, the results converge in describing the tendency of the molecule to favor stable conformations governed by intramolecular interactions (in particular, the expected optimization between steric repulsion and conjugation of pi systems). However, significant solvent effects (whose "absolute" magnitude is actually difficult to assess, due to a certain "method-dependence" of the results) have been also detected.
authors.affiliation: Dipartimento di Chimica, Università della Calabria, 87036 Rende (CS), Italy. giorgio.celebre@unical.it
authors.forename: Giorgio
authors.initials: G
authors.lastname: Celebre
authors.forename: Giorgio
authors.initials: G
authors.lastname: Cinacchi
authors.forename: Giuseppina
authors.initials: G
authors.lastname: De Luca
authors.forename: Barbara M
authors.initials: BM
authors.lastname: Giuliano
authors.forename: Francesca
authors.initials: F
authors.lastname: Iemma
authors.forename: Sonia
authors.initials: S
authors.lastname: Melandri
mesh_terms: D003198:Computer Simulation; D005740:Gases; D008958:Models, Molecular; D008968:Molecular Conformation; D012996:Solutions; D013057:Spectrum Analysis; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D005740:Gases; D012996:Solutions; D013454:Sulfoxides; C417240:methyl phenyl sulfoxide