title: Characterization of 2,5-diaryl-1,3,4-oxadiazolines by multinuclear magnetic resonance and density functional theory calculations. Investigation on a case of very remote Hammett correlation.
abstract: Two series of 2,5-diaryl-1,3,4-oxadiazolines have been studied by multinuclear magnetic resonance and density functional theory calculations. A full NMR spectroscopic characterization has been performed and excellent remote Hammett correlations (sigma(p) or sigma(p)+) have been found for para substitution in the two aryl rings through at least 11 bonds, notwithstanding the presence in the path of atoms that should act as insulators and a lack of correlation for some of the intermediate atoms. The computational investigation on the electronic delocalization, performed with the ACID (anisotropy of the induced current density) method, reveals indeed that electrons are delocalized in almost the entire molecule despite the presence of the insulators.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario, S.S. 554, Bivio per Sestu, I-09042 Monserrato (CA), Italy. cerioni@unica.it
authors.forename: Giovanni
authors.initials: G
authors.lastname: Cerioni
authors.forename: Elias
authors.initials: E
authors.lastname: Maccioni
authors.forename: Maria Cristina
authors.initials: MC
authors.lastname: Cardia
authors.forename: Sara
authors.initials: S
authors.lastname: Vigo
authors.forename: Francesca
authors.initials: F
authors.lastname: Mocci
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D055601:Organic Chemistry Phenomena; D010069:Oxadiazoles / Q000737:chemistry*
chemical_list: D010069:Oxadiazoles; C012466:oxadiazon