Molecular structure, vibration properties and quantum chemical calculations of 4-(chloromethyl)-7-methoxycoumarin and 4-(chloromethyl)-7-methyl-coumarin

Main Article Content

Feride Akman
Kamuran Sarac

Abstract

Objective: A series polymer of polystyrene (PS), which doped with potassium biborate (PS-K2B4O7) and 7-hydroxy-4-methylcoumarin (PS-7H4MC) was prepared by solvent casting method.


Material and Methods: All polymeric materials were characterized by Fourier transform infrared spectroscopy (FTIR). Besides, the molecular optimization of polymeric materials was determined using density functional theory (DFT) in ground state. To predict the reactive regions of polymeric materials, the molecular electrostatic potential (MEP) was investigated using theoretical calculations. Cytotoxicity potentials of different concentrations (0 to 320 mg/L) of metabolites on the cultured human blood cells were determined via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) analyses. In addition, chromosomal aberrations (CA) and micronuclei (MN) tests were scored as genetic endpoints.


Results: The FTIR analysis confirmed the presence of polystyrene polymers dopping with potassium biborate and 7-hydroxy-4-methylcoumarin. The MEP maps showed that the negative potential sites were on oxygen atoms.  The results of MTT and LDH analysis showed that PS-K2B4O7 and PS-7H4MC caused significant decreases of cell viability in a clear dose-dependent manner.  


Conclusion: cytogenetic results of this study revealed that these polymers neither induced CA nor MN formations. Potassium biborate and 7-hydroxy-4-methylcoumarin doped polystyrene polymers demonstrated ameliorative potential against toxic effects by PS on cultured human peripheral blood lymphocytes in our experimental conditions.

Article Details

How to Cite
Akman, F., & Sarac, K. (2016). Molecular structure, vibration properties and quantum chemical calculations of 4-(chloromethyl)-7-methoxycoumarin and 4-(chloromethyl)-7-methyl-coumarin. Natural Science and Discovery, 2(2), 26–35. Retrieved from https://natscidiscovery.com/index.php/nsd/article/view/37
Section
Research Article

References

Sarıkaya EK, Dereli Ö, Erdoğdu Y, Güllüoğlu MT. Molecular structure and vibrational spectra of 7-Ethoxycoumarin by density functional method. Journal of Molecular Structure. 2013;1049: 220-226.
Koparir M, Orek C, Koparir P, Sarac K. Synthesis, experimental, theoretical characterization and biological activities of 4-ethyl-5-(2-hydroxyphenyl)-2H-1, 2, 4-triazole-3 (4H)-thione. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2013; 105: 522-531.
Kumar S, Saini A, Sandhu JS. LiBr-Mediated, solvent free von Pechmann reaction: facile and efficient method for the synthesis of 2H-chromen-2-ones. Arkivoc. 2007;15: 18-23.
Mannekutla JR, Mulimani BG, Inamdar SR. Solvent effect on absorption and fluorescence spectra of coumarin laser dyes: evaluation of ground and excited state dipole moments. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008; 69(2): 419-426.
Christie RM, Lui CH. Studies of fluorescent dyes: part 1. An investigation of the electronic spectral properties of substituted coumarins.Dyes and Pigments. 1999; 42(1): 85-93.
Von Pechmann H, Duisberg C. Ueber die verbindungen der phenole mit acetessigäther. Berichte der deutschen chemischen Gesellschaft. 1883; 16(2):2119-2128.
Adams R, Bockstahler TE. Preparation and reactions of o-hydroxycinnamic acids and esters. Journal of the American Chemical Society. 1952; 74(21): 5346-5348.
Johnson JR. The Perkin reaction and related reactions. Organic Reactions.1942.
Shriner RL. The reformatsky reaction, Organic reactions. 1942.
Yavari I, Hekmat-Shoar R, Zonouzi A. A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt.Tetrahedron Letters. 1998; 39(16): 2391-2392.
Palafox MA, Rastogi VK, Tanwar RP, Mittal L. 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. 2003; 59(11): 2473-2486.
Ten GN, Nechaev VV, Pankratov AN, Berezin VI, Baranov VI. 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. 2010; 51(5): 854-861.
Szczesniak M, Nowak MJ, Szczepaniak K, Chin S, Scott I, Person WB. Matrix isolation studies of nucleic acid constituents—III. 1-Methyluracil, 3-methyluracil and 1, 3-dimethyluracil monomers. Spectrochimica Acta Part A: Molecular Spectroscopy. 1985; 41(1): 223-235.
Çırak Ç, Koç N. Molecular structure and effects of intermolecular hydrogen bonding on the vibrational spectrum of trifluorothymine, an antitumor and antiviral agent. Journal of molecular modeling. 2012; 18(9): 4453-4464.
Mohan S, Sundaraganesan N, Mink J. FTIR and Raman studies on benzimidazole. Spectrochimica Acta Part A: Molecular Spectroscopy. 1991; 47(8): 1111-1115.
Palafox MA, Tardajos G, Guerrero-Martínez A, Rastogi VK, Mishra D, Ojha SP, Kiefer W. FT-IR, FT-Raman spectra, density functional computations of the vibrational spectra and molecular geometry of biomolecule 5-aminouracil. Chemical Physics. 2007; 340(1): 17-31.
Jamróz MH, Dobrowolski JC, Brzozowski R. Vibrational modes of 2, 6-, 2, 7-, and 2, 3-diisopropylnaphthalene. A DFT study. Journal of molecular structure. 2006; 787(1): 172-183.
Singh JS. FTIR and Raman spectra and fundamental frequencies of biomolecule: 5-methyluracil (thymine). Journal of Molecular Structure. 2008; 876(1): 127-133.
Çırak Ç, Sert Y, Ucun F. 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. 2012; 92: 406-414.
Akman F. Spectroscopic investigation, HOMO–LUMO energies, natural bond orbital (NBO) analysis and thermodynamic properties of two-armed macroinitiator containing coumarin with DFT quantum chemical calculations.Canadian Journal of Physics. 2016; 94(6): 583-593.