Research Article
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Year 2023, , 177 - 182, 30.06.2023
https://doi.org/10.22399/ijcesen.1255460

Abstract

References

  • [l] J-Na Zhang, B. Zhang and J-J. Shen, (2017). The optical properties of dinitrobenzoic acid isomers in the tarahertz and infrared regions. J. Infrared Milim. Waves 36(5);536-542. DOI: 10.11972/j.issn.1001-9014.2017.05.005
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  • [10] D. Tiana, C. Zenga, H. Wanga, Xianming Chenga, Y. Zhenga, C. Xiangd, K. Lia and X. Zhu. (2017). Effect of transition metal Fe adsorption on CeO2(110) surface in themethane activation and oxygen vacancy formation: a density functional theory study” Appl. Surf. Sci., 416;547-564. DOI: 10.1016/j.apsusc.2017.04.028
  • [11] P. Hohenberg and W. Kohn, (1964). Inhomogeneous electron gas Phys. Rev. 136;b864-b871. DOI: 10.1103/PhysRev.136.B864
  • [12] W. Kohn and L.J. Sham, (1965). Self-consistent equations including exchange and correlation effects Phys. Rev., 140;a1133–a1138. https://doi.org/10.1103/PhysRev.140.A1133
  • [13] A. D. Becke, (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A., 38(6);3098-3100. DOI: 10.1103/PhysRevA.38.3098
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  • [16] F. Ucun and S.G. Aydın, (2014). Calculated optimized structures and hyperfine coupling constants of some radical adducts of α-phenyl-N-tert-buthyl nitrone in water and benzene solutions J. Organomet. Chem. 759;27-32. DOI:10.1016/j.jorganchem.2014.02.011.
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EPR Analysis of Dinitrobenzoic Acid Anion Radicals

Year 2023, , 177 - 182, 30.06.2023
https://doi.org/10.22399/ijcesen.1255460

Abstract

EPR hyperfine coupling constants of dinitrobenzoic acid anion radicals were calculated by using (DFT) with the use of B3LYP functional at LanL2DZ, LanL2MB, EPR-II, EPR-III, 6-31+G(d) and 6-31++ G(d,p) basis sets. It was found that LanL2DZ is the best basis set from the correlation graphs between the theoretical and experimental results. Thus, in this set, the hyperfine structures formed EPR spectra and the distributions of the spin density of all the anion radicals were determined. From the optimized structures of all the radicals it was decided whether the nitro groups are out of plane or not. The reason of the different distributions of the spin density on the nitro groups were also investigated by Natural Bond Orbital (NBO) and Mulliken charge analyses. In these analyses, the interactions of the nitro groups with the ring were examined. The NBO analysis the anion radical of 2,4-dinitrobenzoic acid showed that there is a strong O-H…O hydrogen bond interaction (182.8 kcal/mol) between the carboxyl and nitro groups. The simulated EPR spectra of some radicals obtained by EPR Simulator software program were harmoniously given with together their experimental spectra.

References

  • [l] J-Na Zhang, B. Zhang and J-J. Shen, (2017). The optical properties of dinitrobenzoic acid isomers in the tarahertz and infrared regions. J. Infrared Milim. Waves 36(5);536-542. DOI: 10.11972/j.issn.1001-9014.2017.05.005
  • [2] S. E. Barrows, C. J.Cramer, D. G.Truhlar, M. S. Elovitz and E. J. Weber. (1996) Factors controlling regioselectivity in the reduction of polynitroaromatics in aqueous solution. Environ. Sci. Technol. 30(10);3028–3038. DOI: 10.1021/es960004x
  • [3] M. N. Mikhailov, A. S. Mendkoich, M. B. Kuzminski, A. Kapranov and A. I. Rusakov. (2005) Electronic structure of 1.3-dinitrobenzene radical anion; a multi-configurational quantum chemical study. Russian Chem. Bulletin, Internat. Ed. 54;2735-2737. DOI:10.1007/s11172-006-0185-3
  • [4] P. L. Nordio, M. V. Pavan and C.Corvaja. (1964) E.s.r. Spectra of Reduced Mono- and Dinitro-Derivatives of Phenol and Benzoic Acid. Trans. Faraday Soc., 60;1985-1990. DOI: 10.1039/TF9646001985
  • [5] L. H. Piette, P. Ludwig and R. N. Adams. (1962) Electron Paramagnetic Resonance of Aromatic and Aliphatic Nitro Anions in Aqueous Solution” J. Chem. Soc. 84;4212-4215. DOI: 10.1021/ja00881a005
  • [6] P. H. Reiger and G. K. Fraenkel. (1963). Analysis of the Electron Spin Resonance Spectra of Aromatic Nitrosubstituted Anion Radicals J. Chem. Phys., 39; 609-629. DOI:10.1063/1.1734301
  • [7] M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 09, Revision D.01 (Gaussian, Inc., Wallingford, CT, 2009). https://gaussian.com/g09citation/
  • [8] R Dennington. T. Keith and J. Milliam, Gaussview Version 5 (Semichem Inc, Shawnee Mission, KS, 2009). https://gaussian.com/g09citation/
  • [9] Y. Wang, G. Fu, Y. Zhang, X. Xu and H. Wan. (2009) O-atom transfer reaction from N2O to CO: A theoretical investigation” Chem. Phys. Lett., 475;202-207. DOI: 10.1016/j.cplett.2009.05.044.
  • [10] D. Tiana, C. Zenga, H. Wanga, Xianming Chenga, Y. Zhenga, C. Xiangd, K. Lia and X. Zhu. (2017). Effect of transition metal Fe adsorption on CeO2(110) surface in themethane activation and oxygen vacancy formation: a density functional theory study” Appl. Surf. Sci., 416;547-564. DOI: 10.1016/j.apsusc.2017.04.028
  • [11] P. Hohenberg and W. Kohn, (1964). Inhomogeneous electron gas Phys. Rev. 136;b864-b871. DOI: 10.1103/PhysRev.136.B864
  • [12] W. Kohn and L.J. Sham, (1965). Self-consistent equations including exchange and correlation effects Phys. Rev., 140;a1133–a1138. https://doi.org/10.1103/PhysRev.140.A1133
  • [13] A. D. Becke, (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A., 38(6);3098-3100. DOI: 10.1103/PhysRevA.38.3098
  • [14] C. Lee, W. Yang and R.G. Parr, (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37;785-789. DOI: 10.1103/PhysRevB.37.785
  • [15] Ş. Nardali, F. Ucun and M. Karakaya, (2017). Calculated hyperfine coupling constants for 5,5-dimethyl-1-pyrroline N-oxide radical products in water and benzene” Russian J. Phys. Chem. A 91;2137-2148. DOI:10.1134/S0036024417110164
  • [16] F. Ucun and S.G. Aydın, (2014). Calculated optimized structures and hyperfine coupling constants of some radical adducts of α-phenyl-N-tert-buthyl nitrone in water and benzene solutions J. Organomet. Chem. 759;27-32. DOI:10.1016/j.jorganchem.2014.02.011.
  • [17] https://www.eprsimulator.org/isotropic.html
  • [18] W. Yang, R. G. Parr, (1985). Hardness, softness and the Fukui function in the electronic theory of metals and catalysis Proc. Natl. Acad. Sci. 82;6723–6726. https://www.jstor.org/stable/26691
There are 18 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Research Article
Authors

Hüsnü Yolburun 0000-0001-7377-7468

Fatih Ucun 0000-0001-7464-7788

Publication Date June 30, 2023
Submission Date April 26, 2023
Acceptance Date June 23, 2023
Published in Issue Year 2023

Cite

APA Yolburun, H., & Ucun, F. (2023). EPR Analysis of Dinitrobenzoic Acid Anion Radicals. International Journal of Computational and Experimental Science and Engineering, 9(2), 177-182. https://doi.org/10.22399/ijcesen.1255460