Molecular structure and vibrational spectra of 2,6-bis(benzylidene)cyclohexanone: A density functional theoretical study

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 78; no. 1; pp. 113 - 121
• Main Authors: Sajan, D., Udaya Lakshmi, K., Erdogdu, Y., Hubert Joe, I.
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 2011
• Subjects: Conjugation; Crystallography, X-Ray; Cyclohexanones - chemistry; DFT; FT-IR; Models, Chemical; Molecular Conformation; NBO analysis; NIR-FT Raman; Quantum Theory; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis, Raman; Static Electricity; Thermodynamics; Vibration; Vibrational spectra; NIR-FT Raman; FT-IR; DFT; Conjugation; Vibrational spectra; NBO analysis
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2010.09.007

The near-infrared Fourier transform (NIR-FT) Raman and Fourier transform infrared (FT-IR) spectral analyses of 2,6-bis(benzylidene)cyclohexanone (BBC) molecule, a potential drugs for the treatment of P388 leukemia cells, were carried out along with density functional computations. The optimized geometry of BBC using density functional theory shows that the energetically favored chair conformation is not observed for central cyclohexanone ring and is found to possess a nearly ‘half chair’ conformation and shows less expansion of the angles and more rotation about the bonds. The existence of intramolecular C–H⋯O improper, blue-shifted hydrogen bond was investigated by means of the NBO analysis. The lowering of carbonyl stretching vibration can be attributed to the mesomeric effect and the π-orbital conjugation induced by the unsaturation in the α-carbon atoms and co-planarity of the (–CH C–(C O)–C CH–) group.