The intramolecular interactions in some aromatic compounds

Abstract

A series of 1, 8-peribridged naphthalenes was synthesized; their molecular and electronic structures were studied. The measured CSC angle is the smallest bridging angle yet recorded for a SAPN derivative. The electronic structure of two isomeric dibromonaphthalenes was investigated. The analysis of O -orbital and halogen lone pair ionization energies enabled us to determine the magnitude of bromine-bromine intramolecular interactions, through-bond and through-space type interactions. The crystal structure of 8-bromo-1-naphthaldehyde-p-tosylhydrazone was studied. The hydrazone and naphthyls units are twisted away from each other by 35B: due to the steric repulsion between bromine and hydrogen. The crystal packing is dominated by NHb "b "b "O hydrogen bonding and aryl(naphthalene) ring stacking.(8-bromonaphthalen-1-yl)methyl 8-bromo-1-naphthoate was synthesized and studied. The plane of the ester group is almost perpendicular to the planes of the two aromatic rings. The anti conformation of the two naphthalene rings indicates the ester is unsuitable for photo-induced decarboxylation process.