Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013, Article ID 712130, 16 pages
http://dx.doi.org/10.1155/2013/712130
Research Article

NLO and NBO Analysis of Sarcosine-Maleic Acid by Using HF and B3LYP Calculations

Sakarya Üniversitesi, Fen Edebiyat Fakültesi Fizik Bölümü, 54140 Adapazarı, Turkey

Received 26 June 2012; Accepted 25 July 2012

Academic Editor: Didier Siri

Copyright © 2013 N. Günay 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. P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, John Wiley & Sons, New York, NY, USA, 1991.
  2. F. Meyers, S. R. Marder, B. M. Pierce, and J. L. Brédas, “Electric field modulated nonlinear optical properties of donor—Acceptor polyenes: sum-over-states investigation of the relationship between molecular polarizabilities (α, β, and γ) and bond length alternation,” Journal of the American Chemical Society, vol. 116, no. 23, pp. 10703–10714, 1994. View at Google Scholar · View at Scopus
  3. K. Mandal, T. Kar, P. K. Nandi, and S. P. Bhattacharyya, “Theoretical study of the nonlinear polarizabilities in H2N and NO2 substituted chromophores containing two hetero aromatic rings,” Chemical Physics Letters, vol. 376, no. 1-2, pp. 116–124, 2003. View at Publisher · View at Google Scholar · View at Scopus
  4. P. K. Nandi, K. Mandal, and T. Kar, “Effect of structural changes in sesquifulvalene on the intramolecular charge transfer and nonlinear polarizations—a theoretical study,” Chemical Physics Letters, vol. 381, no. 1-2, pp. 230–238, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. J. P. Foster and F. Weinhold, “Natural hybrid orbitals,” Journal of the American Chemical Society, vol. 102, no. 24, pp. 7211–7218, 1980. View at Google Scholar · View at Scopus
  6. A. E. Reed, L. A. Curtiss, and F. Weinhold, “Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint,” Chemical Reviews, vol. 88, no. 6, pp. 899–926, 1988. View at Google Scholar · View at Scopus
  7. L. Pauling, “The nature of the chemical bond. Application of results obtained from the quantum mechanics and from a theory of paramagnetic susceptibility to the structure of molecules,” Journal of the American Chemical Society, vol. 53, no. 4, pp. 1367–1400, 1931. View at Google Scholar · View at Scopus
  8. J. C. Slater, “Directed valence in polyatomic molecules,” Physical Review, vol. 37, no. 5, pp. 481–489, 1931. View at Publisher · View at Google Scholar · View at Scopus
  9. A. Mostad and S. Natarajan, “Crystal and molecular structure of sarcosine,” Acta chemica Scandinavica, vol. 43, no. 10, pp. 1004–1006, 1989. View at Google Scholar · View at Scopus
  10. S. C. Bhattacharyya and N. N. Saha, “Crystal and molecular structure of disarcosine hydrobromide,” Journal of Crystal and Molecular Structure, vol. 8, no. 5, pp. 209–215, 1978. View at Publisher · View at Google Scholar · View at Scopus
  11. S. C. Bhattacharyya and N. N. Saha, “Crystal and molecular structure of sarcosine hydrochloride,” Journal of Crystal and Molecular Structure, vol. 8, no. 3, pp. 105–113, 1978. View at Publisher · View at Google Scholar · View at Scopus
  12. M. T. Averbuch-Pouchot, “Crystal structure of a new telluric acid adduct: Te(OH)6· 2(CH3NHCH2COOH),” Zeitschrift für Kristallographie, vol. 183, pp. 285–291, 1988. View at Google Scholar
  13. M. T. Averbuch-Pouchot, “Crystal structure of N-methylglycinium mono-hydrogen-phosphite, (CH3NH2CH2COOH)(HPO3H),” Zeitschrift für Kristallographie, vol. 207, pp. 149–150, 1993. View at Google Scholar
  14. M. T. Averbuch-Pouchot, A. Durif, and J. C. Guitel, “Structures of β-alanine, dl-alanine and sarcosine monophosphates,” Acta Crystallographica C, vol. 44, pp. 1968–1972, 1988. View at Google Scholar
  15. R. V. Krishnakumar, M. S. Nandhini, and S. Natarajan, “Sarcosinium Oxalate Monohydrate,” Acta Crystallographica C, vol. 54, no. IUC9800063, 1998. View at Google Scholar
  16. S. Guha, “The crystal and molecular structure of bis(sarcosinato)nickel(II) dehydrate,” Acta Crystallographica B, vol. 29, pp. 2167–2170, 1973. View at Google Scholar
  17. N. Mishima, K. Itoh, and E. Nakamura, “Structure of calcium chloride-sarcosine (1/3), CaCl2.3C3H7NO2, in the ferroelectric phase,” Acta Crystallographica C, vol. 40, pp. 1824–1827, 1984. View at Google Scholar
  18. M. Ilczyszyn, D. Godzisz, and M. M. Ilczyszyn, “Sarcosine-maleic acid (1 : 1) crystal: structure, 13C NMR and vibrational properties, protonation character,” Spectrochimica Acta A, vol. 59, no. 8, pp. 1815–1828, 2003. View at Publisher · View at Google Scholar · View at Scopus
  19. A. Meister, Biochemistry of Amino Acids, Academic Press, New York, NY, USA, 2nd edition, 1965.
  20. M. N. G. James and G. J. B. Williams, “A refinement of the crystal structure of maleic acid,” Acta Crystallographica B, vol. 30, pp. 1249–1257, 1974. View at Google Scholar
  21. T. Nakajima-Kambe, T. Nozue, M. Mukouyama, and T. Nakahara, “Bioconversion of maleic acid to fumaric acid by Pseudomonas alcaligenes strain XD-1,” Journal of Fermentation and Bioengineering, vol. 84, no. 2, pp. 165–168, 1997. View at Publisher · View at Google Scholar · View at Scopus
  22. V. Balachandran, A. Lakshmi, and A. Janaki, “Vibrational spectroscopic studies and Natural Bond Orbital analysis of 4,6-dichloro-2-(methylthio)pyrimidine based on density functional theory,” Spectrochimica Acta A, vol. 81, pp. 1–7, 2011. View at Publisher · View at Google Scholar · View at Scopus
  23. C. J. John, M. Amalanathan, A. R. Twinkle, P. Srinivasan, and I. H. Joe, “Vibrational spectra and first order hyperpolarizability studies of dimethyl amino pyridinium 4-nitrophenolate 4-nitrophenol,” Spectrochimica Acta A, vol. 81, pp. 151–161, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. V. Mukherjee, N. P. Singh, and R. A. Yadav, “Vibrational fundamentals and natural bond orbitals analysis of some tri-fluorinated benzonitriles in ground state,” Spectrochimica Acta A, vol. 81, pp. 609–619, 2011. View at Publisher · View at Google Scholar · View at Scopus
  25. D. Avci, “The consistency analysis of different semiempirical calculations on second- And third-order nonlinear optical properties of donor-acceptor chromophores containing α-cyan,” Spectrochimica Acta A, vol. 77, no. 3, pp. 665–672, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. V. Arjunan, S. T. Govindaraja, S. Sakiladevi, M. Kalaivani, and S. Mohan, “Spectroscopic, electronic structure and natural bond orbital analysis of o-fluoronitrobenzene and p-fluoronitrobenzene: a comparative study,” Spectrochimica Acta A, vol. 84, no. 1, pp. 196–209, 2011. View at Publisher · View at Google Scholar · View at Scopus
  27. D. Sajan, L. Joseph, N. Vijayan, and M. Karabacak, “Natural bond orbital analysis, electronic structure, non-linear properties and vibrational spectral analysis of l-histidinium bromide monohydrate: a density functional theory,” Spectrochimica Acta A, vol. 81, pp. 85–98, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. D. Avci, “Second and third-order nonlinear optical properties and molecular parameters of azo chromophores: semiempirical analysis,” Spectrochimica Acta A, vol. 82, pp. 37–43, 2011. View at Publisher · View at Google Scholar · View at Scopus
  29. D. Avci, A. Başoğlu, and Y. Atalay, “Ab initio HF and DFT calculations on an organic non-linear optical material,” Structural Chemistry, vol. 21, no. 1, pp. 213–219, 2010. View at Publisher · View at Google Scholar · View at Scopus
  30. S. Sebastian, N. Sundaraganesan, B. Karthikeiyan, and V. Srinivasan, “Quantum mechanical study of the structure and spectroscopic (FT-IR, FT-Raman, 13C, 1H and UV), rst order hyperpolarizabilities, NBO and TD-DFT analysis of the 4-methyl-2-cyanobiphenyl,” Spectrochimica Acta A, vol. 78, no. 2, pp. 590–600, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. D. Avci, H. Cömert, and Y. Atalay, “Ab initio Hartree-Fock calculations on linear and second-order nonlinear optical properties of new acridine-benzothiazolylamine chromophores,” Journal of Molecular Modeling, vol. 14, no. 2, pp. 161–169, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. Z. Zhou, D. Du, Y. Xing, and S. U. M. Khan, “Calculation of the energy of activation in the electron transfer reaction not involving the bond rupture the electrode,” Journal of Molecular Structure, vol. 505, pp. 247–255, 2000. View at Publisher · View at Google Scholar · View at Scopus
  33. Z. Zhou, A. Fu, and D. Du, “Studies on density functional theory for the electron-transfer reaction mechanism between M–C6H6 and M+–C6H6 complexes in the gas phase,” International Journal of Quantum Chemistry, vol. 78, no. 3, pp. 186–194, 2000. View at Google Scholar · View at Scopus
  34. E. F. Healy and A. Holder, “An evaluation of AM1 calculated vibrational frequencies,” Journal of Molecular Structure, vol. 281, no. 2-3, pp. 141–156, 1993. View at Google Scholar · View at Scopus
  35. A. P. Scott and L. Radom, “Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors,” Journal of Physical Chemistry, vol. 100, no. 41, pp. 16502–16513, 1996. View at Google Scholar · View at Scopus
  36. R. G. Pearson, “Absolute electronegativity and Hardness correlated with molecular orbital theory,” Proceeding of the National Academy of Sciences, vol. 83, pp. 8440–8441, 1986. View at Google Scholar
  37. A. K. Chandra and T. Uchimara, “Hardness profile: a criticcal study,” The Journal of Physical Chemistry A, vol. 105, pp. 3578–3582, 2001. View at Google Scholar
  38. J. Chocholoušová, V. Špirko, and P. Hobza, “First local minimum of the formic acid dimer exhibits simultaneously red-shifted O–HO and improper blue-shifted C–HO hydrogen bonds,” Physical Chemistry Chemical Physics, vol. 6, no. 1, pp. 37–41, 2004. View at Publisher · View at Google Scholar · View at Scopus
  39. E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold, NBO Version 3.1.
  40. M. J. Frisch, G. W. Trucks, and H. B. Schlegel, Gaussian 09, Revision A.1, Gaussian, Wallingford Conn, USA, 2009.
  41. M. Szafran, A. Komasa, and E. Bartoszak-Adamska, “Crystal and molecular structure of 4-carboxypiperidinium chloride (4-piperidinecarboxylic acid hydrochloride),” Journal of Molecular Structure, vol. 827, no. 1–3, pp. 101–107, 2007. View at Publisher · View at Google Scholar · View at Scopus
  42. R. Dennington, T. Keith, and J. Millam, GaussView, Version 5, Semichem, Shawnee Mission, Kan, USA, 2009.
  43. K. Rajagopal, M. S. Nandhini, R. V. Krishnakumar, A. Mostad, and S. Natarajan, “Sarcosinium maleate at 123 K,” Acta Crystallographica E, vol. 58, pp. 478–480, 2002. View at Google Scholar
  44. R. V. Krishnakumar, M. Subha Nandhini, and S. Natarajan, “Sarcosinium tartrate,” Acta Crystallographica C, vol. 57, no. 2, pp. 165–166, 2001. View at Publisher · View at Google Scholar · View at Scopus
  45. S. Franklin and T. Balasubramanian, “Salts of maleic and fumaric acids with oxine: the role of isomeric acids in hydrogen-bonding patterns,” Acta Crystallographica C, vol. 65, no. 2, pp. 58–61, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. J. Zhang, X. Hou, W. Bu et al., “Hydrogen-bonded 1,2-bis(4-pyridyl)-ethylene and maleic acid,” Acta Crystallographica C, vol. 58, no. 11, pp. 663–664, 2002. View at Publisher · View at Google Scholar · View at Scopus
  47. L. Goodman and R. R. Sauers, “Diffuse functions in natural bond orbital analysis,” Journal of Computational Chemistry, vol. 28, no. 1, pp. 269–275, 2007. View at Publisher · View at Google Scholar · View at Scopus
  48. E. Scrocco and J. Tomasi, “Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potential,” Advances in Quantum Chemistry, vol. 11, pp. 115–193, 1979. View at Publisher · View at Google Scholar · View at Scopus
  49. F. J. Luque, J. M. López, and M. Orozco, “Perspective on “Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects”,” Theoretical Chemistry Accounts, vol. 103, no. 3-4, pp. 343–345, 2000. View at Google Scholar · View at Scopus
  50. N. Okulik and A. H. Jubert, “Theoretical analysis of the reactive sites of non–steroidal anti–inflammatory drugs,” Internet Electronic Journal of Molecular Design, vol. 4, pp. 17–30, 2005. View at Google Scholar
  51. C. Hansch, A. Leo, and R. W. Taft, “A survey of hammett substituent constants and resonance and field parameters,” Chemical Reviews, vol. 91, no. 2, pp. 165–195, 1991. View at Google Scholar · View at Scopus
  52. T. R. Felthouse, J. C. Burnett, B. Horrell, M. J. Mummey, and Y. J. Kuo, Huntsman Petrochemical Corporation Austin Laboratories, North Lamar Boulevard, Austin, Tex, USA, 2001.
  53. O. Castellano, M. Giffard, M. Chrysos et al., “Theoretical study of the linear and nonlinear optical properties of polyacene-thiolate and polyphenylene-thiolate anions,” Journal of Molecular Structure: THEOCHEM, vol. 716, no. 1–3, pp. 1–9, 2005. View at Publisher · View at Google Scholar · View at Scopus
  54. C. A. Van Walree, O. Franssen, A. W. Marsman, M. C. Flipse, and L. W. Jenneskens, “Second-order nonlinear optical properties of stilbene, of benzylideneaniline and azobenzene derivatives. The effect of π-bridge nitrogen insertion on the first hyperpolarizability,” Journal of the Chemical Society, vol. 2, no. 4, pp. 799–807, 1997. View at Google Scholar · View at Scopus
  55. L. Jensen and P. T. Van Duijnen, “The first hyperpolarizability of p-nitroaniline in 1,4-dioxane: a quantum mechanical/molecular mechanics study,” Journal of Chemical Physics, vol. 123, no. 7, Article ID 074307, 2005. View at Publisher · View at Google Scholar · View at Scopus
  56. P. Sałek, O. Vahtras, T. Helgaker, and H. Ågren, “Density-functional theory of linear and nonlinear time-dependent molecular properties,” Journal of Chemical Physics, vol. 117, no. 21, pp. 9630–9645, 2002. View at Publisher · View at Google Scholar · View at Scopus
  57. M. Stähelin, D. M. Burland, and J. E. Rice, “Solvent dependence of the second order hyperpolarizability in p-nitroaniline,” Chemical Physics Letters, vol. 191, no. 3-4, pp. 245–250, 1992. View at Google Scholar · View at Scopus
  58. F. L. Huyskens, P. L. Huyskens, and A. P. Persoons, “Solvent dependence of the first hyperpolarizability of p-nitroanilines: differences between nonspecific dipole-dipole interactions and solute-solvent H-bonds,” Journal of Chemical Physics, vol. 108, no. 19, pp. 8161–8171, 1998. View at Google Scholar · View at Scopus
  59. H. Li, K. Han, X. Shen et al., “The first hyperpolarizabilities of hemicyanine cationic derivatives studied by finite-field (FF) calculations,” Journal of Molecular Structure: THEOCHEM, vol. 767, no. 1–3, pp. 113–118, 2006. View at Publisher · View at Google Scholar · View at Scopus
  60. D. P. Shelton and J. E. Rice, “Measurements and calculations of the hyperpolarizabilities of atoms and small molecules in the gas phase,” Chemical Reviews, vol. 94, no. 1, pp. 3–29, 1994. View at Google Scholar · View at Scopus
  61. B. F. Levine, “Donor-acceptor charge transfer contributions to the second order hyperpolarizability,” Chemical Physics Letters, vol. 37, no. 3, pp. 516–520, 1976. View at Google Scholar · View at Scopus
  62. L. T. Cheng, W. Tam, S. R. Marder, A. E. Stiegman, G. Rikken, and C. W. Spangler, “Experimental investigations of organic molecular nonlinear optical polarizabilities. 2. A study of conjugation dependences,” Journal of Physical Chemistry, vol. 95, no. 26, pp. 10643–10652, 1991. View at Google Scholar · View at Scopus
  63. B. A. S. Mendis and K. M. N. De Silva, “A comprehensive study of linear and non-linear optical properties of novel charge transfer molecular systems,” Journal of Molecular Structure: THEOCHEM, vol. 678, no. 1-3, pp. 31–38, 2004. View at Publisher · View at Google Scholar · View at Scopus
  64. Y. Daoudi and P. J. Bonifassi, “Nonlinear optical properties of push pull molecules grafted onto chloromethylstyrene. Hyperpolarizabilities of first- And second-order obtained by PM3, AM1 and MNDO methods. Correlation of EFISH measures on side-chain polymer with quantum chemistry results,” Journal of Molecular Structure: THEOCHEM, vol. 451, no. 3, pp. 277–293, 1998. View at Google Scholar · View at Scopus
  65. L. T. Cheng, W. Tam, S. H. Stevenson, G. R. Meredith, G. Rikken, and S. R. Marder, “Experimental investigations of organic molecular nonlinear optical polarizabilities. 1. Methods and results on benzene and stilbene derivatives,” Journal of Physical Chemistry, vol. 95, no. 26, pp. 10631–10643, 1991. View at Google Scholar · View at Scopus
  66. S. P. Karna, P. N. Prasad, and M. Dupuis, “Nonlinear optical properties of p-nitroaniline: an ab initio time-dependent coupled perturbed Hartree-Fock study,” The Journal of Chemical Physics, vol. 94, no. 2, pp. 1171–1181, 1991. View at Google Scholar · View at Scopus
  67. P. Kaatz, E. A. Donley, and D. P. Shelton, “A comparison of molecular hyperpolarizabilities from gas and liquid phase measurements,” Journal of Chemical Physics, vol. 108, no. 3, pp. 849–856, 1998. View at Google Scholar · View at Scopus