Publication

Abstract : The 1H and 13C NMR spectra of five 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-one O-methoxy oximes were recorded. The chemical shifts, conformation, orientation of the aryl groups and effect of 1, 3 allylic interactions were analyzed using COSY, NOESY, HSQC and HMBC spectral data. These studies propose that the reported compounds exhibit twin-chair conformations with the axial and equatorial orientation of the aryl groups. The proposed conformation and aryl group orientations are unambiguously confirmed by single-crystal X-ray diffraction analysis. In the crystal, one C−H···Cl hydrogen-bonding and two C−H···π interactions were present between the asymmetric unit. Many types of C−H···Cl, C−H···π and π···π intermolecular interactions interconnects two asymmetric units to form a three-dimensional framework. The analysis of Hirshfeld surface and fingerprint plots indicates the dominance of Cl···H (36.6 %) and H···H (36.3 %) contacts to the overall packing arrangement. The molecular reactivity and electron density descriptors HOMO, LUMO, MEP and Fukui functions are calculated using DFT calculation of the studied O-methoxy oximes 3a–3e.