UMYMFOR   05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
congresos y reuniones científicas
Título:
Conformational and long-range anisotropy study of ?V? shaped molecules: DFT calculations and NMR assignment of Tröger?s base diamide.
Autor/es:
TRUPP, LEANDRO; LAURELLA, SERGIO; TETTAMANZI, M. CRISTINA; BRUTTOMESSO, ANDREA
Lugar:
Santiago
Reunión:
Congreso; 10th Congress of the World Association of Theoretical and Computational Chemists .; 2014
Institución organizadora:
World Association of Theoretical and Computational Chemists
Resumen:
Building blocks with well defined rigid structures are very convenient in organic synthesis, as they allow controlling the disposition of different substituents in predictable geometries. This molecules arouse both practical and theoretical interest, and are very attractive for their application in molecular recognition, drug development, bioorganic and supramolecular chemistry and as materials for optical and optoelectronical devices. Tröger?s base is one of the most used compounds of this kind, because it adopts a rigid ?V? shaped geometry with the aromatic rings almost perpendicular to each other, that causes the spatial proximity of substituents far away in the connectivity and their mutual influence. In our laboratory, we work in the potential application of Tröger?s base derivatives in different fields, such us the synthesis of compounds with interesting intervalence properties or as ligands in metal complexation, and as a result of this study we synthesized diformamide 1. Formamides often present NMR (Nuclear Magnetic Resonance) distinguishable conformers, due to the slow rotation of the amide bond, but the complex array of signals in 1H and 13C NMR spectra of 1 ?also dependent both of the solvent and the temperature- suggested that it presents special anisotropic properties arising from some communication between the two amides. In this work, we present the synthesis and complete analysis of NMR spectra of 1, through a computational study of this compound?s conformational behaviour using the DFT/B3LYP/6-31G(d,p) method and GIAO calculations with implicit solvent considerations.