Yıl 2018, Cilt 22, Sayı 6, Sayfalar 1638 - 1647 2018-12-01

The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives

Serpil Eryılmaz [1]

87 245

In this study, global reactivity descriptors such as ionization potential, electron affinity, electronegativity, chemical hardness, softness and electrophilicity index of norbornadiene derivatives which include some halogen atoms and atom groups, have been investigated with DFT/BPV86/B3LYP/B3PW91 methods with 6-31G(d,p) basis set. To determine the non-linear optical behaviours of the structures, the total dipole moment,  polarizability,and first-order hyperpolarizabilityvalues have been examined at the same theoretical level. It has been determined that thiol-bonded groups on comparison with others have a much better NLO material property. In addition, the potentials of the structures as drug-active compounds have been inspected with Lipinski’s rule of 5 and bioactivity scores. Thiol and hydroxyl-bonded groups have a good drug-likeness and bioactivity score relative to the others.

Global reactivity descriptors, NLO, DFT, Lipinski’s rule of 5
  • P. Hohenberg and W. Kohn. “Inhomogeneous electron gas.” Physical Review, vol. 136, pp. B864-B871, 1964. W. Kohn and L. J. Sham. “Self-Consistent Equations Including Exchange and Correlation Effects.” Physical Review, vol. 140, pp. A1133-A1138, 1965. R. G. Parr and W. Yang. “Density-functional theory of atoms and molecules.” Oxford Univ. Press, Oxford, UK. 1989. W. Koch and M. C. Holthausen. “A Chemist’s Guide to Density Functional Theory.” John Wiley & Sons, New York, 2001.
  • R. G. Parr and R. G. Pearson. “Absolute hardness: companion parameter to absolute electronegativity.” Journal of the American Chemical Society, vol. 105, pp. 7512-7516, 1983.
  • P. Geerlings, F. De Proft and W. Langenaeker. “Conceptual Density Functional Theory.” Chemical Reviews. vol. 103, pp. 1793−1873, 2003.
  • P. W. Ayers et al., “Fukui Function”, in Chemical Reactivity Theory, A Density Functional View, P. K. Chattaraj Ed, New York, USA CRC Press, Taylor&Francis Group, 2009, pp. 255-265.
  • P. N. Prasad and D. J. Williams. “Introduction to Nonlinear Optical Effects in Organic Molecules and Polymers”, New York, USA, Wiley, 1991, pp. 272-273.
  • J. Zyss and D. S. Chemla, “Quadratic Nonlinear Optics and Optimization of the Second Order Nonlinear, optical Response of Molecular Crystals”, in Nonlinear Optical Properties of Organic Molecules and Crystals. D. S. Chemla and J. Zyss Eds., New York, USA, Academic Press, 1987. pp. 272-273
  • D. Sajan, D, H. Joe, V.S. Jayakumar and J. Zaleski. “Structural and Electronic Contributions to Hyperpolarizability in methyl p-hydroxy benzoate”. Journal of Molecular Structure, vol.785, pp. 43-53, 2006.
  • H. P. Gümüş and Y. Atalay. “3-hidroksi-4-hidroksimiinometil-5-hidroksimetil-1, 2-dimetilpiridinyum iyodid molekülünün geometrik yapısının incelenmesi.” Sakarya Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 21, no. 3, pp. 564-571, 2017.
  • Z. Zonghua, C. Debeng, W. Xiu and L. Deming. “Preparation and nonlinear optical properties of organic and polymeric materials.” Ferroelectrics, vol.101, pp.141-142, 1990.
  • S. Eryılmaz, M. Gül, E. İnkaya, Ö. İdil and N. Özdemir. “Synthesis, crystal structure analysis, spectral characterization, quantum chemical calculations, antioxidant and antimicrobial activity of 3-(4-chlorophenyl)-3a, 4, 7, 7a-tetrahydro-4, 7-methanobenzo [d] isoxazole.” Journal of Molecular Structure, vol. 1122, pp. 219-233, 2016.
  • K. Mesci, S. Eryılmaz, M. Gül and E. İnkaya. “The investigation of spectroscopic and theoretical methods of bisisoxaoline derivative of norbornadiene.” Anadolu University of Sciences & Technology-A: Applied Sciences & Engineering, vol. 17, no. 4, pp. 641-659, 2016.
  • S. H. Vosko, L. Wilk and M Nusair. “Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis.” Canadian Journal of Physics, vol. 58, no.8, pp. 1200-1211, 1980.
  • a)A. D. Becke. “Density-functional exchange-energy approximation with correct asymptotic behavior.” Journal of Chemicals Physics, vol. 38, pp. 3098-3100, 1988. b) A. D. Becke. “Density-Functional Thermochemistry. I. The Effect of the Exchange-Only Gradient Correction.” Journal of Chemicals Physics, vol. 96, pp. 2155-2160, 1992. c) A.D. Becke. “Density functional thermochemistry III. The role of exact exchange.” Journal of Chemicals Physics, vol. 98, pp. 5648-5652, 1993.
  • J. P. Perdew, K. Burke and Y. Wang. “Generalized gradient approximation for the exchange-correlation hole of a many-electron system.” Physical Review. B, Condensed Matter, vol. 54, pp. 16533-16539, 1996.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian 09 (Gaussian, Inc., Wallingford CT, 2009).
  • GaussView, Version 5, R. Dennington, T. A. Keith and J. M. Millam, Semichem Inc., Shawnee Mission, KS, 2009.
  • T. Koopmans. “Ordering of wave functions and eigenenergies to the individual electrons of an atom.” Physica. vol.1, no.1, pp. 104-113, 1933.
  • R. G. Parr and R. G. Pearson. “Absolute hardness: companion parameter to absolute electronegativity.” Journal of the American Chemical Society, vol.105, no.26, pp. 7512-7516, 1983.
  • R. S. Mulliken. “A new electron affinity scale; together with data on valence states and on valence ionization potentials and electron affinities.” The Journal of Chemical Physics, vol. 2, no.11, pp. 782-793, 1934.
  • a) R. G. Pearson. “Hard and soft acids and bases.” Journal of the American Chemical Society, vol. 85, no.22, pp. 3533-3539, 1963. b) R. G. Pearson. “Hard and soft acids and bases, HSAB, part 1: Fundamental principles.” Journal of Chemical Education, vol. 45, no.9, p581, 1968. c) R. G. Pearson. “Maximum chemical and physical hardness.” Journal of Chemical Education, vol. 76, no. 2, p267, 1999.
  • A. Vektariene, G. Vektaris and J. Svoboda. “A theoretical approach to the nucleophilic behavior of benzofused thieno [3, 2-b] furans using DFT and HF based reactivity descriptors.” Arkivoc: Online Journal of Organic Chemistry, vol.vii, pp. 311-329, 2009.
  • R. G. Parr and R. G. Pearson. “Absolute hardness: companion parameter to absolute electronegativity.” Journal of the American Chemical Society, vol. 105, no.26, pp. 7512-7516, 1983.
  • R. G. Pearson. “Absolute electronegativity and hardness correlated with molecular orbital theory.” Proceedings of the National Academy of Sciences, vol. 83, no.22, pp. 8440-8441, 1986.
  • P. K. Chattaraj and D. R. Roy. “Update 1 of: Electrophilicity index.” Chemical Reviews, vol. 107, no.9, pp PR46–PR74, 2007.
  • J. Hernández-Paredes, D. Glossman-Mitnik, A. Duarte-Moller and N. Flores-Holguín. “Theoretical calculations of molecular dipole moment, polarizability, and first hyperpolarizability of glycine–sodium nitrate.” Journal of Molecular Structure: THEOCHEM. vol. 905, no.1, pp. 76-80, 2009.
  • J. Prashanth, G. Ramesh, J. L. Naik, J. K. Ojha, B. V. Reddy and G. R. Rao. “Molecular Structure, Vibrational Analysis and First Order Hyperpolarizability of 4-Methyl-3-Nitrobenzoic Acid Using Density Functional Theory.” Optics and Photonics Journal. vol. 5, no. 03, p. 91, 2015.
  • a) D. A. Kleinman. “Nonlinear dielectric polarization in optical media.” Physical Review. vol. 126, no. 6, pp.1977-1979, 1962. b) S. Ramalingam, M. Karabacak, S. Periandy, N. Puviarasan and D. Tanuja. “Spectroscopic (infrared, Raman, UV and NMR) analysis, Gaussian hybrid computational investigation (MEP maps/HOMO and LUMO) on cyclohexanone oxime.” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. vol. 96, pp. 207-220, 2012.
  • C. A. Lipinski. “Lead-and drug-like compounds: the rule-of-five revolution.” Drug Discovery Today: Technologies. vol. 1, no.4, pp. 337-341, 2004.
  • B. Jayaram, T. Singh, G. Mukherjee, A. Mathur, S. Shekhar and V. Shekhar, "Sanjeevini: a freely accessible web-server for target directed lead molecule discovery", BMC Bioinformatics. vol. 13, S7, 2012.
  • P. Ertl, B. Rohde and P. Selzer. “Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties.” Journal of Medicinal Chemistry.vol. 43, pp. 3714-3717, 2000.
  • C. A. Lipinski, F. Lombardo, B. W. Dominy and P.J. Feeney. “Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings.” Advanced Drug Delivery Reviews. vol. 23, pp. 4-25, 1997.
  • D. F. Veber, S.R. Johnson, H.-Y. Cheng, B.R. Smith, K.W. Ward and K.D. Kopple. “Molecular properties that influence the oral bioavailability of drug candidates.” Journal of Medicinal Chemistry. vol.45, pp. 2615-2623, 2002.
  • C. G. Zhan, J. A. Nichols and D. A. Dixon, “Ionization potential, electron affinity, electronegativity, hardness, and electron excitation energy: molecular properties from density functional theory orbital energies.” The Journal of Physical Chemistry A. vol. 107, no. 20, pp. 4184-4195, 2003.
  • N. Günay, H. Pir and Y. Atalay.” L-asparaginyum pikrat molekülünün spektroskopik özelliklerinin teorik olarak incelenmesi.” SAÜ Fen Edebiyat Dergisi, vol.1, pp.15-32, 2011.
  • V. P. Gupta. Principles and Applications of Quantum Chemistry. Waltham, USA, Academic Press, 2015, pp. 430-431.
  • D. Pegu and N. B. Singh. “Quantum Chemical Calculations of Molecular Structure, Electronic, Thermodynamic and Non-linear optical properties of 2-amino-3-nitro-6-methyl pyridine.” International Journal of Advanced Research. vol. 1, no.9, 2013.
  • S. Singh, A. K. Gupta and A. Verma. “Molecular Properties and Bioactivity score of the Aloe vera antioxidant compounds – in order to lead finding” Research Journal of Pharmaceutical, Biological and Chemical Sciences. vol. 4, no.2, pp.876-81, 2013.
Birincil Dil en
Konular Fizik, Uygulamalı
Yayımlanma Tarihi December 2018
Dergi Bölümü Araştırma Makalesi
Yazarlar

Orcid: orcid.org/0000-0002-0935-4644
Yazar: Serpil Eryılmaz (Sorumlu Yazar)
Ülke: Turkey


Bibtex @araştırma makalesi { saufenbilder359837, journal = {Sakarya University Journal of Science}, issn = {1301-4048}, eissn = {2147-835X}, address = {Sakarya Üniversitesi}, year = {2018}, volume = {22}, pages = {1638 - 1647}, doi = {10.16984/saufenbilder.359837}, title = {The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives}, key = {cite}, author = {Eryılmaz, Serpil} }
APA Eryılmaz, S . (2018). The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives. Sakarya University Journal of Science, 22 (6), 1638-1647. DOI: 10.16984/saufenbilder.359837
MLA Eryılmaz, S . "The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives". Sakarya University Journal of Science 22 (2018): 1638-1647 <http://www.saujs.sakarya.edu.tr/issue/31266/359837>
Chicago Eryılmaz, S . "The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives". Sakarya University Journal of Science 22 (2018): 1638-1647
RIS TY - JOUR T1 - The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives AU - Serpil Eryılmaz Y1 - 2018 PY - 2018 N1 - doi: 10.16984/saufenbilder.359837 DO - 10.16984/saufenbilder.359837 T2 - Sakarya University Journal of Science JF - Journal JO - JOR SP - 1638 EP - 1647 VL - 22 IS - 6 SN - 1301-4048-2147-835X M3 - doi: 10.16984/saufenbilder.359837 UR - http://dx.doi.org/10.16984/saufenbilder.359837 Y2 - 2018 ER -
EndNote %0 Sakarya University Journal of Science The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives %A Serpil Eryılmaz %T The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives %D 2018 %J Sakarya University Journal of Science %P 1301-4048-2147-835X %V 22 %N 6 %R doi: 10.16984/saufenbilder.359837 %U 10.16984/saufenbilder.359837
ISNAD Eryılmaz, Serpil . "The theoretical investigation of global reactivity descriptors, NLO behaviours and bioactivity scores of some norbornadiene derivatives". Sakarya University Journal of Science 22 / 6 (Aralık 2018): 1638-1647. http://dx.doi.org/10.16984/saufenbilder.359837