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 center dot center dot center dot 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 pi-orbital conjugation induced by the unsaturation in the alpha-carbon atoms and co-planarity of the (-CH=C-(C=O)-C=CH-) group. (C) 2010 Elsevier B.V. All rights reserved.