Vibrational spectroscopic and molecular docking study of 2-Benzylsulfanyl-4-[(4-methylphenyl)-sulfanyl]-6-pentylpyrimidine- 5-carbonitrile, a potential chemotherapeutic agent Nadia G. Haress a , Ali A. El-Emam a,b , Omar A. Al-Deeb a , C. Yohannan Panicker c,⇑ , Abdulaziz A. Al-Saadi d , Christian Van Alsenoy e , Javeed Ahmad War f , S.K. Srivastava f a Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia b King Abdullah Institute for Nanotechnology (KAIN), King Saud University, Riyadh 11451, Saudi Arabia c Department of Physics, TKM College of Arts and Science, Kollam, Kerala, India d Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia e Department of Chemistry, University of Antwerp, B2610 Antwerp, Belgium f Department of Chemistry, Dr. H. S. Gour Central University, Sagar, M.P. 470003, India highlights  IR, Raman spectra and NBO analysis were reported.  The wavenumbers are calculated theoretically using Gaussian09 software.  The wavenumbers are assigned using PED analysis.  The geometrical parameters are in agreement with XRD data.  Molecular docking is reported. graphical abstract article info Article history: Received 21 July 2014 Received in revised form 6 August 2014 Accepted 24 August 2014 Available online 4 September 2014 Keywords: DFT Sulfanyl Pyrimidine Molecular docking Hyperpolarizability abstract FT-IR and FT-Raman spectra of 2-Benzylsulfanyl-4-[(4-methylphenyl)-sulfanyl]-6-pentylpyrimidine-5- carbonitrile were recorded and analyzed. The structure of the molecule has been optimized and the struc- tural characteristics have been determined by density functional theory. The geometrical parameters (DFT) are in agreement with the XRD results. HOMO and LUMO and other chemical properties are reported. Nonlinear optical properties are reported. A detailed molecular picture of the title compound and its interactions were obtained from NBO analysis. The negative (red and yellow) regions of the MEP are related to electrophilic reactivity and the positive (blue) regions to nucleophilic reactivity, as shown in the MEP plot and the title compound has several possible sites, C„N, N atom of pyrimidine ring and sulfur atoms for electrophilic attack. From the molecular docking studies it is clear that the title com- pound binds at the catalytic site of the substrate by weak non-covalent interactions most prominent of which are H-bonding, p–p, alkyl–p, and amide–p interactions. Ó 2014 Elsevier B.V. All rights reserved. http://dx.doi.org/10.1016/j.saa.2014.08.112 1386-1425/Ó 2014 Elsevier B.V. All rights reserved. ⇑ Corresponding author. Tel.: +91 9895370968. E-mail address: cyphyp@rediffmail.com (C.Y. Panicker). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 137 (2015) 569–580 Contents lists available at ScienceDirect Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy journal homepage: www.elsevier.com/locate/saa