Theoretical Study of the Geometry of Dibenzoazepine Analogues

Abstract

The geometry of dibenzoazepine analogues—typical multifunctional drugs—was investigated to find the geometrical parameters sensitive to the substitution of the central seven-membered ring. Exploration of the crystal structure database (CSD) shows that the geometrical parameter sensitive to the substitution of the carbon atom distance of the central ring not included in the aromatic rings to the plane through the carbon atoms common for the central ring and the aromatic side rings. Presence of the double bond in the central ring was reflected in its partial aromaticity expressed by the HOMED parameter. Some derivatives of 5H-dibenzo[b,f]azepine with flat conformation of the central ring are characterized by mobility of the electron density comparable to the mobility in the aromatic side rings. Influence of the surrounding on the investigated compounds was confirmed by comparison of the optimized molecules and the molecules in the crystal state where the packing forces can influence the molecular geometry.

Keywords

• 5<i>H</i>-dibenzo[b,f]azepine
• 10,11-dihydro-5<i>H</i>-dibenzo[b,f]azepine
• 5<i>H</i>-dibenzo[a,d][7]annulene
• 10,11-dihydro-5<i>H</i>-dibenzo[a,d][7]annulene
• molecular structure
• aromaticity