Table of Contents Author Guidelines Submit a Manuscript
Journal of Spectroscopy
Volume 2016, Article ID 5396439, 15 pages
http://dx.doi.org/10.1155/2016/5396439
Research Article

Spectroscopic Investigations and DFT Calculations on 3-(Diacetylamino)-2-ethyl-3H-quinazolin-4-one

1Department of Physics, Faculty of Art & Sciences, Bozok University, 66100 Yozgat, Turkey
2Sorgun Vocational School, Bozok University, 66100 Yozgat, Turkey
3Department of Physics, Faculty of Art & Sciences, Süleyman Demirel University, 32100 Isparta, Turkey
4Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, P.O. Box 10219, Riyadh 11433, Saudi Arabia
5School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK

Received 23 October 2015; Accepted 28 January 2016

Academic Editor: Christoph Krafft

Copyright © 2016 Yusuf Sert et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. V. Alagarsamy, V. R. Solomon, and K. Dhanabal, “Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents,” Bioorganic and Medicinal Chemistry, vol. 15, no. 1, pp. 235–241, 2007. View at Publisher · View at Google Scholar · View at Scopus
  2. R. Rohini, P. M. Reddy, K. Shanker, A. Hu, and V. Ravinder, “Antimicrobial study of newly synthesized 6-substituted indolo[1,2-c]quinazolines,” European Journal of Medicinal Chemistry, vol. 45, no. 3, pp. 1200–1205, 2010. View at Publisher · View at Google Scholar · View at Scopus
  3. V. Gupta, S. K. Kashaw, V. Jatav, and P. Mishra, “Synthesis and antimicrobial activity of some new 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2- styrylquinazoline-4(3H)-ones,” Medicinal Chemistry Research, vol. 17, no. 2, pp. 205–211, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. V. Chandregowda, A. K. Kush, and G. C. Reddy, “Synthesis and in vitro antitumor activities of novel 4-anilinoquinazoline derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 7, pp. 3046–3055, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. M. F. Abdel-Megeed, B. E. Badr, M. M. Azaam, and G. A. El-Hiti, “Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates,” Bioorganic and Medicinal Chemistry, vol. 20, no. 7, pp. 2252–2258, 2012. View at Publisher · View at Google Scholar · View at Scopus
  6. S. Sasmal, G. Balaji, H. R. K. Reddy et al., “Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists,” Bioorganic & Medicinal Chemistry Letters, vol. 22, no. 9, pp. 3157–3162, 2012. View at Publisher · View at Google Scholar · View at Scopus
  7. M. S. Malamas and J. Millen, “Quinazolineacetic acids and related analogues as aldose reductase inhibitors,” Journal of Medicinal Chemistry, vol. 34, no. 4, pp. 1492–1503, 1991. View at Publisher · View at Google Scholar · View at Scopus
  8. J. Ma, B. Han, J. Song et al., “Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles in water without any catalyst,” Green Chemistry, vol. 15, no. 6, pp. 1485–1489, 2013. View at Publisher · View at Google Scholar · View at Scopus
  9. L. Xu, Y. Jiang, and D. Ma, “Synthesis of 3-substituted and 2,3-disubstituted quinazolinones via Cu-catalyzed aryl amidation,” Organic Letters, vol. 14, no. 4, pp. 1150–1153, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. M. Adib, E. Sheikhi, and H. R. Bijanzadeh, “One-pot three-component synthesis of 4(3H)-quinazolinones from benzyl halides, isatoic anhydride, and primary amines,” Synlett, vol. 23, no. 1, Article ID D13011ST, pp. 85–88, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. K. Smith, G. A. El-Hiti, and M. F. Abdel-Megeed, “Regioselective lithiation of chiral 3-acylamino-2-alkylquinazolin-4(3H)- ones: application in synthesis,” Synthesis, no. 13, pp. 2121–2130, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. G. A. El-Hiti, “A simple procedure for the side-chain substitution of 2-alkyl-3H-quinazoline-4-thiones: application in synthesis,” Synthesis, no. 3, pp. 363–368, 2004. View at Publisher · View at Google Scholar
  13. G. A. El-Hiti, “Application of organolithium in organic synthesis: a simple and convenient procedure for the synthesis of more complex 6-substituted 3H-quinazolin-4-ones,” Monatshefte fur Chemie, vol. 135, no. 3, pp. 323–331, 2004. View at Publisher · View at Google Scholar · View at Scopus
  14. G. A. El-Hiti, A. S. Hegazy, M. H. Alotaibi, and M. D. Ajarim, “Reactions of organolithium reagents with quinazoline derivatives,” Arkivoc, vol. 2012, no. 7, pp. 35–78, 2012. View at Google Scholar · View at Scopus
  15. K. Smith, G. A. El-Hiti, and S. A. Hegazy, “A simple and convenient procedure for lithiation and side-chain substitution of 2-alkyl-4-(methylthio)quinazolines and 2-alkyl-4-methoxyquinazolines,” Synthesis, no. 17, pp. 2951–2961, 2005. View at Publisher · View at Google Scholar
  16. G. M. Sheldrick, “Phase annealing in SHELX-90: direct methods for larger structures,” Acta Crystallographica Section A: Foundations of Crystallography, vol. 46, no. 6, pp. 467–473, 1990. View at Publisher · View at Google Scholar
  17. G. M. Sheldrick, SHELXS-97, Program for Crystal Structure Refinement, Universität Göttingen, Göttingen, Germany, 1997.
  18. M. A. Palafox, V. K. Rastogi, R. P. Tanwar, and L. Mittal, “Vibrational frequencies and structure of 2-thiouracil by Hartree-Fock, post-Hartree-Fock and density functional methods,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 59, no. 11, pp. 2473–2486, 2003. View at Publisher · View at Google Scholar · View at Scopus
  19. G. N. Ten, V. V. Nechaev, A. N. Pankratov, V. I. Berezin, and V. I. Baranov, “Effect of hydrogen bonding on the structure and vibrational spectra of the complementary pairs of nucleic acid bases. II. adenine-thymine,” Journal of Structural Chemistry, vol. 51, no. 5, pp. 854–861, 2010. View at Publisher · View at Google Scholar · View at Scopus
  20. Ç. Çırak and N. Koç, “Molecular structure and effects of intermolecular hydrogen bonding on the vibrational spectrum of trifluorothymine, an antitumor and antiviral agent,” Journal of Molecular Modeling, vol. 18, no. 9, pp. 4453–4464, 2012. View at Publisher · View at Google Scholar · View at Scopus
  21. M. A. Palafox, G. Tardajos, A. Guerrero-Martínez et al., “FT-IR, FT-Raman spectra, density functional computations of the vibrational spectra and molecular geometry of biomolecule 5-aminouracil,” Chemical Physics, vol. 340, no. 1–3, pp. 17–31, 2007. View at Publisher · View at Google Scholar · View at Scopus
  22. J. S. Singh, “FTIR and Raman spectra and fundamental frequencies of biomolecule: 5-methyluracil (thymine),” Journal of Molecular Structure, vol. 876, no. 1–3, pp. 127–133, 2008. View at Publisher · View at Google Scholar · View at Scopus
  23. M. H. Jamróz, J. C. Dobrowolski, and R. Brzozowski, “Vibrational modes of 2,6-, 2,7-, and 2,3-diisopropylnaphthalene. A DFT study,” Journal of Molecular Structure, vol. 787, no. 1–3, pp. 172–183, 2006. View at Publisher · View at Google Scholar · View at Scopus
  24. Ç. Çırak, Y. Sert, and F. Ucun, “Experimental and computational study on molecular structure and vibrational analysis of a modified biomolecule: 5-Bromo-2′-deoxyuridine,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 92, no. 6, pp. 406–414, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. Y. Zhao and D. G. Truhlar, “The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals,” Theoretical Chemistry Accounts, vol. 120, no. 1–3, pp. 215–241, 2008. View at Publisher · View at Google Scholar · View at Scopus
  26. K. Helios, R. Wysokiński, A. Pietraszko, and D. Michalska, “Vibrational spectra and reinvestigation of the crystal structure of a polymeric copper(II)-orotate complex, [Cu(μ-HOr)(H2O) 2]n: the performance of new DFT methods, M06 and M05-2X, in theoretical studies,” Vibrational Spectroscopy, vol. 55, no. 2, pp. 207–215, 2011. View at Publisher · View at Google Scholar · View at Scopus
  27. J. Gu, J. Wang, and J. Leszczynski, “Stacking and H-bonding patterns of dGpdC and dGpdCpdG: performance of the M05-2X and M06-2X Minnesota density functionals for the single strand DNA,” Chemical Physics Letters, vol. 512, no. 1–3, pp. 108–112, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. K. H. Lemke and T. M. Seward, “Thermodynamic properties of carbon dioxide clusters by M06-2X and dispersion-corrected B2PLYP-D theory,” Chemical Physics Letters, vol. 573, no. 6, pp. 19–23, 2013. View at Publisher · View at Google Scholar · View at Scopus
  29. E. I. Paulraj and S. Muthu, “Spectroscopic studies (FTIR, FT-Raman and UV), potential energy surface scan, normal coordinate analysis and NBO analysis of (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl) piperidine-3,4,5-triol by DFT methods,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 108, no. 5, pp. 38–49, 2013. View at Publisher · View at Google Scholar · View at Scopus
  30. U. Yadava, M. Singh, and M. Roychoudhury, “Gas-phase conformational and intramolecular π-π interaction studies on some pyrazolo[3,4-d]pyrimidine derivatives,” Computational and Theoretical Chemistry, vol. 977, no. 1–3, pp. 134–139, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. C. N. Ramachandran and E. Ruckenstein, “Density functional theoretical studies of the isomers of croconic acid and their dimers,” Computational and Theoretical Chemistry, vol. 973, no. 1–3, pp. 28–32, 2011. View at Publisher · View at Google Scholar · View at Scopus
  32. Y. Sert, Ç. Çırak, and F. Ucun, “Vibrational analysis of 4-chloro-3-nitrobenzonitrile by quantum chemical calculations,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 107, no. 4, pp. 248–255, 2013. View at Publisher · View at Google Scholar · View at Scopus
  33. A. Frish, A. B. Nielsen, and A. J. Holder, Gauss View User Manual, Gaussian Inc, Pittsburg, Pa, USA, 2001.
  34. W. H. James, E. G. Buchanan, C. W. Müller et al., “Evolution of amide stacking in larger γ-peptides: triamide H-bonded cycles,” Journal of Physical Chemistry A, vol. 115, no. 47, pp. 13783–13798, 2011. View at Publisher · View at Google Scholar · View at Scopus
  35. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 03, Revision D.01, Gaussian, Wallingford, Conn, USA, 2004.
  36. M. H. Jamróz, Vibrational Energy Distribution Analysis VEDA 4, 2004.
  37. M. H. Jamróz, “Vibrational energy distribution analysis (VEDA): scopes and limitations,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 114, no. 10, pp. 220–230, 2013. View at Publisher · View at Google Scholar · View at Scopus
  38. H. Arslan and Ö. Algül, “Vibrational spectrum and assignments of 2-(4-methoxyphenyl)-1H-benzo[d]imidazole by ab initio Hartree-Fock and density functional methods,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 70, no. 1, pp. 109–116, 2008. View at Publisher · View at Google Scholar · View at Scopus
  39. C. Irak, S. Demir, F. Ucun, and O. Ubuk, “Experimental and theoretical study on the structure and vibrational spectra of β-2-aminopyridinium dihydrogenphosphate,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 79, no. 3, pp. 529–532, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. G. A. El-Hiti, K. Smith, A. S. Hegazy, M. D. Ajarim, and B. M. Kariuki, “Crystal structure of 2-[4-(methylsulfanyl)quinazolin-2-yl]-1-phenylethanol,” Acta Crystallographica Section E: Crystallographic Communications, vol. 70, no. 11, p. o1101, 2014. View at Publisher · View at Google Scholar
  41. C. Y. Panicker, H. T. Varghese, K. R. Ambujakshan et al., “Vibrational spectra and computational study of 3-amino-2-phenyl quinazolin-4(3H)-one,” Journal of Molecular Structure, vol. 963, no. 2-3, pp. 137–144, 2010. View at Publisher · View at Google Scholar · View at Scopus
  42. C. Y. Panicker, H. T. Varghese, K. R. Ambujakshan et al., “Ab initio and density functional theory studies on vibrational spectra of 3-{[(4-methoxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one,” European Journal of Chemistry, vol. 1, no. 1, pp. 37–43, 2010. View at Google Scholar
  43. J. P. Jasinski, J. A. Golen, A. S. Praveen, H. S. Yathirajan, and B. Narayana, “Methyl 3,5-di­bromo-2-di­acetyl­amino­benzoate,” Acta Crystallographica Section E: Crystallographic Communications, vol. 67, no. 9, p. o2503, 2011. View at Publisher · View at Google Scholar
  44. C.-L. He, Z.-M. Du, Z.-Q. Tang, X.-M. Cong, and L.-Q. Meng, “N-(1-Diacetyl­amino-1H-tetra­zol-5-yl)acetamide,” Acta Crystallographica, Section E: Crystallographic Communications, vol. 65, part 8, article o1902, 2009. View at Publisher · View at Google Scholar
  45. G. Socrates, Infrared and Raman Characteristic Group Frequencies: Tables and Charts, John Wiley & Sons, Chichester, UK, 3rd edition, 2004.
  46. C. Y. Panicker, H. T. Varghese, K. R. Ambujakshan et al., “FT-IR and FT-Raman spectra and ab initio calculations of 3-{[(2-hydroxyphenyl) methylene]amino}-2-phenylquinazolin-4(3H)-one,” Journal of Raman Spectroscopy, vol. 40, no. 9, pp. 1262–1273, 2009. View at Publisher · View at Google Scholar
  47. C. Y. Panicker, H. T. Varghese, K. R. Ambujakshan et al., “FT-IR, FT-Raman and DFT calculations of 3-{[(4-fluorophenyl)methylene] amino}-2-phenylquinazolin-4(3H)-one,” Journal of Raman Spectroscopy, vol. 40, no. 5, pp. 527–536, 2009. View at Publisher · View at Google Scholar · View at Scopus
  48. N. P. G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, John Wiley & Sons, New York, NY, USA, 1994.
  49. P. Larkin, Infrared and Raman Spectroscopy; Principles and Spectral Interpretation, Elsevier, Waltham, Mass, USA, 1st edition, 2011.
  50. C. Y. Panicker, H. T. Varghese, M. Nair, K. Raju, M. Laila, and G. M. Warrier, “Vibrational spectroscopic studies and ab initio calculations of 3-nitroacetanilide,” Oriental Journal of Chemistry, vol. 25, no. 3, pp. 643–647, 2009. View at Google Scholar · View at Scopus
  51. I. Yalçin, E. Şener, T. Özden, S. Özden, and A. Akin, “Synthesis and microbiological activity of 5-methyl-2-[p-substituted phenyl]benzoxazoles,” European Journal of Medicinal Chemistry, vol. 25, no. 8, pp. 705–708, 1990. View at Publisher · View at Google Scholar · View at Scopus
  52. R. Saxena, L. D. Kandpal, and G. N. Mathur, “Synthesis and characterization of poly(benzobisthiazole)s derived from halogenated phthalic acid and isophthalic acid,” Journal of Polymer Science, Part A: Polymer Chemistry, vol. 40, no. 22, pp. 3959–3966, 2002. View at Publisher · View at Google Scholar · View at Scopus
  53. R. M. Silverstein and F. X. Webster, Spectrometric Identification of Organic Compound, John Wiley & Sons, Singapore, 6th edition, 2003.
  54. J. M. Engasser and C. Horvath, “Electrostatic effects on the kinetics of bound enzymes,” Biochemical Journal, vol. 145, no. 3, pp. 431–435, 1975. View at Publisher · View at Google Scholar · View at Scopus
  55. S. Kundoo, A. N. Banerjee, P. Saha, and K. K. Chattopadhyay, “Synthesis of crystalline carbon nitride thin films by electrolysis of methanol-urea solution,” Materials Letters, vol. 57, no. 15, pp. 2193–2197, 2003. View at Publisher · View at Google Scholar · View at Scopus
  56. J. Coates and R. A. Meyers, Introduction to Infrared Spectrum. A Practical Approach, John Wiley & Sons, Chichester, UK, 2000.
  57. M. Pagannone, B. Fornari, and G. Mattei, “Molecular structure and orientation of chemisorbed aromatic carboxylic acids: surface enhanced Raman spectrum of benzoic acid adsorbed on silver sol,” Spectrochimica Acta Part A: Molecular Spectroscopy, vol. 43, no. 5, pp. 621–625, 1987. View at Publisher · View at Google Scholar · View at Scopus
  58. S. R. Kumar, N. Vijay, K. Amarendra, P. Onkar, and S. Leena, “Theoretical studies on the isomers of quinazolinone by first principles,” Research Journal of Recent Sciences, vol. 1, no. 3, pp. 11–18, 2012. View at Google Scholar
  59. D. L. Pavia, G. M. Lampman, and G. S. Kriz, Introduction to Spectroscopy, Harcourt College Publishers, 2001.
  60. E. Kavitha, N. Sundaraganesan, S. Sebastian, and M. Kurt, “Molecular structure, anharmonic vibrational frequencies and NBO analysis of naphthalene acetic acid by density functional theory calculations,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 77, no. 3, pp. 612–619, 2010. View at Publisher · View at Google Scholar · View at Scopus
  61. K. Chaitanya, “Molecular structure, vibrational spectroscopic (FT-IR, FT-Raman), UV-vis spectra, first order hyperpolarizability, NBO analysis, HOMO and LUMO analysis, thermodynamic properties of benzophenone 2,4-dicarboxylic acid by ab initio HF and density functional method,” Spectrochimica Acta—Part A: Molecular and Biomolecular Spectroscopy, vol. 86, pp. 159–173, 2012. View at Publisher · View at Google Scholar · View at Scopus
  62. E. Kavitha, N. Sundaraganesan, and S. Sebastian, “Molecular structure, vibrational spectroscopic and HOMO, LUMO studies of 4-nitroaniline by density functional method,” Indian Journal of Pure & Applied Physics, vol. 48, no. 1, pp. 20–30, 2010. View at Google Scholar · View at Scopus
  63. A. Jayaprakash, V. Arjunan, and S. Mohan, “Vibrational spectroscopic, electronic and quantum chemical investigations on 2,3-hexadiene,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 81, no. 1, pp. 620–630, 2011. View at Publisher · View at Google Scholar · View at Scopus
  64. M. Govindarajan, M. Karabacak, A. Suvitha, and S. Periandy, “FT-IR, FT-Raman, ab initio, HF and DFT studies, NBO, HOMO-LUMO and electronic structure calculations on 4-chloro-3-nitrotoluene,” Spectrochimica Acta—Part A: Molecular and Biomolecular Spectroscopy, vol. 89, pp. 137–148, 2012. View at Publisher · View at Google Scholar · View at Scopus