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Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule

Year 2022, Volume: 26 Issue: 5, 879 - 891, 20.10.2022

Emine Babur Şaş Songül Çifçi Mustafa Kurt

https://doi.org/10.16984/saufenbilder.1100391
Cited By: 1

Abstract

After first determining the optimized geometry of the 1H-benzimidazole-2-carboxylic acid monohydrate (1HBCM) molecule using the B3LYP/6-311+ + G (d, p) basis set, we investigated the spectroscopic properties, electronic properties and optical band gap of the molecule. We presented the fitted values of the vibrational frequencies of the molecule both as a table and as a spectrum and compared them with the experimental data. While the band gap energy (E) values of the molecule were calculated using HOMO and LUMO energies, the optical band gap (Eg) values of the molecule were obtained from the Tauc equation. We have given the Eg values of the molecule calculated for direct and indirect transmission by comparing them with the experimental data. In the article, we have also calculated and presented the data of the 1HBCM molecule such as MEP, Mulliken, and DOS.

Keywords

FT-Raman FT–IR optical band gap DFT MEP.

Project Number

TBY.A4.19.001

References

  • [1] W. Akhtar, M. F. Khan, G. Verma, M. Shaquiquzzaman, M. A. Rizvi, S. H. Mehdi, M. Akhter, M. M. Alam, “Therapeutic evolution of benzimidazole derivatives in the last quinquennial period” European Journal of Medicinal Chemistry, vol. 126, no. 27, pp. 705-753, 2017.
  • [2] F. Fei, Z. Zhou, “New Substituted Benzimidazole Derivatives: a Patent Review (2010 - 2012)” Expert Opinion on Therapeutic Patents, vol. 23, pp. 1157–1179, 2013.
  • [3] M. Wang, X. Han, Z. Zhou, “New Substituted Benzimidazole Derivatives: A Patent Review (2013 - 2014)” Expert Opinion on Therapeutic, Patents no. 25, pp. 595–612, 2015.
  • [4] S. O. Podunavac-Kuzmonovic, L. M. Leovac, N. U. Perisicjanjic, J. Rogan, J. Balaz, “Complexes of cobalt(II), zinc(II) and copper(II) with some newly synthesized benzimidazole derivatives and their antibacterial activity” Journal of the Serbian Chemical Society, vol. 64, pp. 381-388, 1999.
  • [5] F. Vogetle, “Supramolecular Chemistry: An Introduction”, Wiley, New York, 1991.
  • [6] K. Takahasi, K. Horino, T. Komura, K. Murata, “Photovoltaic Properties of Porphyrin Thin Films Mixed with o-Chloranil” Bulletin of the Chemical Society of Japan, vol. 66, no. 3, pp. 733–738, 1993.
  • [7] R. S. Mulliken, “Structures of Complexes Formed by Halogen Molecules with Aromatic and with Oxygenated Solvents” Journal of the American Chemical Society, vol. 72, pp. 600–608, 1950.
  • [8] A. M. Mansour, “Coordination behavior of sulfamethazine drug towards Ru(III) and Pt(II) ions: Synthesis, spectral, DFT, magnetic, electrochemical and biological activity studies”, Inorganica Chimica Acta vol. 394, pp. 436–445, 2013.
  • [9] J. Tauc, A. Menth, “States in the gap” Journal of Non-Crystalline Solids, vol. 569, pp. 8–10, 1972.
  • [10] E. Babur Sas, M. Kurban, B. Gündüz, M.Kurt, “Photophysical, spectroscopic properties and electronic structure of BND: Experiment and theory”, Synthetic Metals, vol. 246, pp. 39-44, 2018.
  • [11] S. Krawczyk, M. Gdaniec, F. Saczewski, “1H-Benzimidazole-2-carboxylic acid monohydrate” Acta Crystallographica Section E, vol. 61 pp. 4185-4187, 2005.
  • [12] E. B. Sas, M. Kurt, M. Karabacak, A. Poiyamozhi, N. Sundaraganesan, “FT-IR, FT-Raman, dispersive Raman, NMR spectroscopic studies and NBO analysis of 2-Bromo-1H-Benzimidazol by density functional method” Journal of Molecular Structure, vol. 1081, pp. 506–518, 2015.
  • [13] E. B. Sas, M. Kurt, “Ft-raman, ft-ir, nmr and dft calculations of 5-bromo-1h benzimidazole” Sakarya University Journal of Science, vol. 1, no. 3, pp. 430-441, 2017.
  • [14] M. Karabacak, E. Kose, A. Atac, E. B. Sas, A. M. Asiri, M. Kurt, “Experimental (FT-IR, FT-Raman, UV–Vis, 1H and 13C NMR) and computational (density functional theory) studies on 3-bromophenylboronic acid” Journal of Molecular Structure, vol. 1076, pp. 358–372, 2014.
  • [15] V. Krishnakumar, R. Ramasamy, “Density functional and experimental studies on the FT-IR and FT-Raman spectra and structure of 2,6-diamino purine and 6-methoxy purine” Spectrochim. Acta A, vol. 69, pp. 8-17, 2008.
  • [16] O. R. Shehab, A. M. Mansour, “Charge transfer complexes of 2-arylaminomethyl-1H-benzimidazole with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone: Experimental and DFT studies”, Journal of Molecular Structure, vol. 1047, pp. 121-135, 2013.
  • [17] N. T. A. Ghani, A. M. Mansour, “Molecular structure of 2-chloromethyl-1H-benzimidazole hydrochloride: Single crystal, spectral, biological studies, and DFT calculations”, Spectrochimica Acta Part A, vol. 86, pp. 605–613, 2012.
  • [18] T. S. Xavier, N. Rashid, I. H. Joe, “Vibrational spectra and DFT study of anticancer active molecule 2-(4-Bromophenyl)-1H-benzimidazole by normal coordinate analysis” Spectrochimica Acta Part A, vol. 78, pp. 319–326, 2011.
  • [19] V. Arjunan, A. Raj, C. V. Mythili, S. Mohan, “Structural, vibrational, electronic investigations and quantum chemical studies of 2-amino-4-methoxybenzothiazole” Journal of Molecular Structure, vol. 1036, pp. 327-340, 2013.
  • [20] G. Varsanyi, “Vibrational Spectra of Benzene Derivatives”, Academic Press: New York, 1969.
  • [21] H. G. Silver, J. L. Wood, “Factors affecting torsional barriers in benzaldehyde derivatives”, Transactions of the Faraday Society, vol. 60, pp. 5-11, 1964.
  • [22] R. Ramasamy, “Analysis of Vibrational Spectra of Pyridoxazinone Based on Density Functional Theory Calculations”, Journal of Applied Spectroscopy, vol. 80, pp. 492–498, 2013.
  • [23] R. Ramasamy, “Vibrational spectroscopic studies of imidazole”, Armenian Journal of Physics, vol. 8, pp. 51-55, 2015.
  • [24] Y. Wang, R. A. Poirier, “Factors that influence the CN stretching frequency in imines”, The Journal of Physical Chemistry A, vol. 101, no. 5, pp. 907–912, 1997.
  • [25] C. Y.Huang, T. Wang, F. Gai, “Temperature dependence of the CN stretching vibration of a nitrile-derivatized phenylalanine in water” Chemical Physics Letters, vol. 371, no. 5–6, pp. 731-738, 2003.
  • [26] I. Fleming, “Frontier Orbitals and Organic Chemical Reactions”, Wiley, London, 1976.
  • [27] R. Hoffman, “Solids and Surfaces: A Chemist’s View of Bonding in Extended Structures”, Wiley- VCH Publisher, Newyork, 1988.
  • [28] W. Kohn, L. J. Sham, “Self-consistent equations including exchange and correlation effects” Physical Review, vol. 140, no. A, pp. 1133-1141, 1965.
  • [29] N. M. O'Boyle, A. L. Tenderholt, K. M. Langner “cclib: a library for package-independent computational chemistry algorithms” Journal of Computational Chemistry, vol. 29, pp. 839-845, 2008.
  • [30] S. Armaković, S. J. Armaković, J .P. Šetrajčić “Hydrogen storage properties of sumanene” International Journal of Hydrogen Energy, vol. 38, pp. 12190-12198, 2013.
  • [31] S. Armaković, S. J.Armaković, J. P. Setrajcic, S. K. Jacimovski, V. Holodkov, “Sumanene and its adsorption properties towards CO, CO2 and NH3 molecules” Journal of Molecular Modeling, vol. 20, pp. 2170-2177, 2014.
  • [32] N. Okulik, A. H. Jubert “Theoretical study on the structure and reactive sites of non-steroidal anti-inflammatory drugs” Journal of Molecular Structure: THEOCHEM, vol. 682, pp. 55-62, 2004.
  • [33] E. Scrocco, J. Tomasi, “Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials” Advances in Quantum Chemistry, vol. 11, pp. 115-193, 1978.
  • [34] H. P. Gümüş, Y. Atalay, “3-hidroksi-4-hidroksimiinometil-5-hidroksimetil-1,2-dimetilpiridinyum iyodid molekülünün geometrik yapısının incelenmesi” Sakarya University Journal of Science Institute, vol. 21, no. 3, pp. 564-571, 2017.
  • [35] J. B. Ott, J. Boerio-Goates, “Chemical Thermodynamics: Advanced Applications, Calculations from Statistical Thermodynamics”, Academic Press, 2000.
  • [36] E. B. Sas, N. Cankaya, M. Kurt, “Synthesis of 2-(bis (cyanomethyl) amino)-2-oxoethyl methacrylate monomer molecule and its characterization by experimental and theoretical methods” Journal of Molecular Structure, vol. 1161, pp. 433-441, 2018.

Year 2022, Volume: 26 Issue: 5, 879 - 891, 20.10.2022

Emine Babur Şaş Songül Çifçi Mustafa Kurt

https://doi.org/10.16984/saufenbilder.1100391
Cited By: 1

Abstract

Supporting Institution

Kırşehir Ahi Evran Üniversitesi

Project Number

TBY.A4.19.001

References

  • [1] W. Akhtar, M. F. Khan, G. Verma, M. Shaquiquzzaman, M. A. Rizvi, S. H. Mehdi, M. Akhter, M. M. Alam, “Therapeutic evolution of benzimidazole derivatives in the last quinquennial period” European Journal of Medicinal Chemistry, vol. 126, no. 27, pp. 705-753, 2017.
  • [2] F. Fei, Z. Zhou, “New Substituted Benzimidazole Derivatives: a Patent Review (2010 - 2012)” Expert Opinion on Therapeutic Patents, vol. 23, pp. 1157–1179, 2013.
  • [3] M. Wang, X. Han, Z. Zhou, “New Substituted Benzimidazole Derivatives: A Patent Review (2013 - 2014)” Expert Opinion on Therapeutic, Patents no. 25, pp. 595–612, 2015.
  • [4] S. O. Podunavac-Kuzmonovic, L. M. Leovac, N. U. Perisicjanjic, J. Rogan, J. Balaz, “Complexes of cobalt(II), zinc(II) and copper(II) with some newly synthesized benzimidazole derivatives and their antibacterial activity” Journal of the Serbian Chemical Society, vol. 64, pp. 381-388, 1999.
  • [5] F. Vogetle, “Supramolecular Chemistry: An Introduction”, Wiley, New York, 1991.
  • [6] K. Takahasi, K. Horino, T. Komura, K. Murata, “Photovoltaic Properties of Porphyrin Thin Films Mixed with o-Chloranil” Bulletin of the Chemical Society of Japan, vol. 66, no. 3, pp. 733–738, 1993.
  • [7] R. S. Mulliken, “Structures of Complexes Formed by Halogen Molecules with Aromatic and with Oxygenated Solvents” Journal of the American Chemical Society, vol. 72, pp. 600–608, 1950.
  • [8] A. M. Mansour, “Coordination behavior of sulfamethazine drug towards Ru(III) and Pt(II) ions: Synthesis, spectral, DFT, magnetic, electrochemical and biological activity studies”, Inorganica Chimica Acta vol. 394, pp. 436–445, 2013.
  • [9] J. Tauc, A. Menth, “States in the gap” Journal of Non-Crystalline Solids, vol. 569, pp. 8–10, 1972.
  • [10] E. Babur Sas, M. Kurban, B. Gündüz, M.Kurt, “Photophysical, spectroscopic properties and electronic structure of BND: Experiment and theory”, Synthetic Metals, vol. 246, pp. 39-44, 2018.
  • [11] S. Krawczyk, M. Gdaniec, F. Saczewski, “1H-Benzimidazole-2-carboxylic acid monohydrate” Acta Crystallographica Section E, vol. 61 pp. 4185-4187, 2005.
  • [12] E. B. Sas, M. Kurt, M. Karabacak, A. Poiyamozhi, N. Sundaraganesan, “FT-IR, FT-Raman, dispersive Raman, NMR spectroscopic studies and NBO analysis of 2-Bromo-1H-Benzimidazol by density functional method” Journal of Molecular Structure, vol. 1081, pp. 506–518, 2015.
  • [13] E. B. Sas, M. Kurt, “Ft-raman, ft-ir, nmr and dft calculations of 5-bromo-1h benzimidazole” Sakarya University Journal of Science, vol. 1, no. 3, pp. 430-441, 2017.
  • [14] M. Karabacak, E. Kose, A. Atac, E. B. Sas, A. M. Asiri, M. Kurt, “Experimental (FT-IR, FT-Raman, UV–Vis, 1H and 13C NMR) and computational (density functional theory) studies on 3-bromophenylboronic acid” Journal of Molecular Structure, vol. 1076, pp. 358–372, 2014.
  • [15] V. Krishnakumar, R. Ramasamy, “Density functional and experimental studies on the FT-IR and FT-Raman spectra and structure of 2,6-diamino purine and 6-methoxy purine” Spectrochim. Acta A, vol. 69, pp. 8-17, 2008.
  • [16] O. R. Shehab, A. M. Mansour, “Charge transfer complexes of 2-arylaminomethyl-1H-benzimidazole with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone: Experimental and DFT studies”, Journal of Molecular Structure, vol. 1047, pp. 121-135, 2013.
  • [17] N. T. A. Ghani, A. M. Mansour, “Molecular structure of 2-chloromethyl-1H-benzimidazole hydrochloride: Single crystal, spectral, biological studies, and DFT calculations”, Spectrochimica Acta Part A, vol. 86, pp. 605–613, 2012.
  • [18] T. S. Xavier, N. Rashid, I. H. Joe, “Vibrational spectra and DFT study of anticancer active molecule 2-(4-Bromophenyl)-1H-benzimidazole by normal coordinate analysis” Spectrochimica Acta Part A, vol. 78, pp. 319–326, 2011.
  • [19] V. Arjunan, A. Raj, C. V. Mythili, S. Mohan, “Structural, vibrational, electronic investigations and quantum chemical studies of 2-amino-4-methoxybenzothiazole” Journal of Molecular Structure, vol. 1036, pp. 327-340, 2013.
  • [20] G. Varsanyi, “Vibrational Spectra of Benzene Derivatives”, Academic Press: New York, 1969.
  • [21] H. G. Silver, J. L. Wood, “Factors affecting torsional barriers in benzaldehyde derivatives”, Transactions of the Faraday Society, vol. 60, pp. 5-11, 1964.
  • [22] R. Ramasamy, “Analysis of Vibrational Spectra of Pyridoxazinone Based on Density Functional Theory Calculations”, Journal of Applied Spectroscopy, vol. 80, pp. 492–498, 2013.
  • [23] R. Ramasamy, “Vibrational spectroscopic studies of imidazole”, Armenian Journal of Physics, vol. 8, pp. 51-55, 2015.
  • [24] Y. Wang, R. A. Poirier, “Factors that influence the CN stretching frequency in imines”, The Journal of Physical Chemistry A, vol. 101, no. 5, pp. 907–912, 1997.
  • [25] C. Y.Huang, T. Wang, F. Gai, “Temperature dependence of the CN stretching vibration of a nitrile-derivatized phenylalanine in water” Chemical Physics Letters, vol. 371, no. 5–6, pp. 731-738, 2003.
  • [26] I. Fleming, “Frontier Orbitals and Organic Chemical Reactions”, Wiley, London, 1976.
  • [27] R. Hoffman, “Solids and Surfaces: A Chemist’s View of Bonding in Extended Structures”, Wiley- VCH Publisher, Newyork, 1988.
  • [28] W. Kohn, L. J. Sham, “Self-consistent equations including exchange and correlation effects” Physical Review, vol. 140, no. A, pp. 1133-1141, 1965.
  • [29] N. M. O'Boyle, A. L. Tenderholt, K. M. Langner “cclib: a library for package-independent computational chemistry algorithms” Journal of Computational Chemistry, vol. 29, pp. 839-845, 2008.
  • [30] S. Armaković, S. J. Armaković, J .P. Šetrajčić “Hydrogen storage properties of sumanene” International Journal of Hydrogen Energy, vol. 38, pp. 12190-12198, 2013.
  • [31] S. Armaković, S. J.Armaković, J. P. Setrajcic, S. K. Jacimovski, V. Holodkov, “Sumanene and its adsorption properties towards CO, CO2 and NH3 molecules” Journal of Molecular Modeling, vol. 20, pp. 2170-2177, 2014.
  • [32] N. Okulik, A. H. Jubert “Theoretical study on the structure and reactive sites of non-steroidal anti-inflammatory drugs” Journal of Molecular Structure: THEOCHEM, vol. 682, pp. 55-62, 2004.
  • [33] E. Scrocco, J. Tomasi, “Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials” Advances in Quantum Chemistry, vol. 11, pp. 115-193, 1978.
  • [34] H. P. Gümüş, Y. Atalay, “3-hidroksi-4-hidroksimiinometil-5-hidroksimetil-1,2-dimetilpiridinyum iyodid molekülünün geometrik yapısının incelenmesi” Sakarya University Journal of Science Institute, vol. 21, no. 3, pp. 564-571, 2017.
  • [35] J. B. Ott, J. Boerio-Goates, “Chemical Thermodynamics: Advanced Applications, Calculations from Statistical Thermodynamics”, Academic Press, 2000.
  • [36] E. B. Sas, N. Cankaya, M. Kurt, “Synthesis of 2-(bis (cyanomethyl) amino)-2-oxoethyl methacrylate monomer molecule and its characterization by experimental and theoretical methods” Journal of Molecular Structure, vol. 1161, pp. 433-441, 2018.
There are 36 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Research Articles
Authors

Emine Babur Şaş 0000-0002-9547-5951

Songül Çifçi 0000-0003-3009-3490

Mustafa Kurt 0000-0001-6040-1189

Project Number TBY.A4.19.001
Publication Date October 20, 2022
Submission Date April 8, 2022
Acceptance Date August 9, 2022
Published in Issue Year 2022 Volume: 26 Issue: 5

Cite

APA Babur Şaş, E., Çifçi, S., & Kurt, M. (2022). Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule. Sakarya University Journal of Science, 26(5), 879-891. https://doi.org/10.16984/saufenbilder.1100391
AMA Babur Şaş E, Çifçi S, Kurt M. Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule. SAUJS. October 2022;26(5):879-891. doi:10.16984/saufenbilder.1100391
Chicago Babur Şaş, Emine, Songül Çifçi, and Mustafa Kurt. “Spectroscopic Characterization and DFT Calculations on 1H-Benzimidazole-2-Carboxylic Acid Monohydrate Molecule”. Sakarya University Journal of Science 26, no. 5 (October 2022): 879-91. https://doi.org/10.16984/saufenbilder.1100391.
EndNote Babur Şaş E, Çifçi S, Kurt M (October 1, 2022) Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule. Sakarya University Journal of Science 26 5 879–891.
IEEE E. Babur Şaş, S. Çifçi, and M. Kurt, “Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule”, SAUJS, vol. 26, no. 5, pp. 879–891, 2022, doi: 10.16984/saufenbilder.1100391.
ISNAD Babur Şaş, Emine et al. “Spectroscopic Characterization and DFT Calculations on 1H-Benzimidazole-2-Carboxylic Acid Monohydrate Molecule”. Sakarya University Journal of Science 26/5 (October 2022), 879-891. https://doi.org/10.16984/saufenbilder.1100391.
JAMA Babur Şaş E, Çifçi S, Kurt M. Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule. SAUJS. 2022;26:879–891.
MLA Babur Şaş, Emine et al. “Spectroscopic Characterization and DFT Calculations on 1H-Benzimidazole-2-Carboxylic Acid Monohydrate Molecule”. Sakarya University Journal of Science, vol. 26, no. 5, 2022, pp. 879-91, doi:10.16984/saufenbilder.1100391.
Vancouver Babur Şaş E, Çifçi S, Kurt M. Spectroscopic Characterization and DFT Calculations on 1H-benzimidazole-2-carboxylic acid monohydrate Molecule. SAUJS. 2022;26(5):879-91.

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