Skip to main content
SpringerLink
Log in

Structural, spectral, and theoretical investigations of 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

The present research work has focused on combined experimental and theoretical studies of one of the biologically important pyrazole-4-carboxylic acid derivatives, viz. 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid (C11H10N2O2). The starting material 5-methyl-1-phenyl-1H-4-pyrazolecarboxylate (1) was obtained by the cyclocondensation of ethyl acetoacetate, N,N-dimethylformamide dimethyl acetal (DMF-DMA), and phenylhydrazine, which upon basic hydrolysis yielded the corresponding acid (2). The target compound (2) was characterized by 1H and 13C NMR (solution in DMSO), Fourier transform infrared (FT-IR) spectroscopy, thermo gravimetric analysis, and by single-crystal X-ray diffraction technique. The single crystals of compound (2) were obtained at room temperature by slow evaporation of ethanol as solvent and crystallized in the space group P2 1/n of monoclinic system. The experimental FT-IR and 1H and 13C NMR chemical shifts have been compared to those calculated by means of density functional theory (DFT) at the B3LYP/TZ2P level of theory. The continuum-like screening model was used for geometry optimization of a single molecule and for subsequent calculations of NMR shielding constants in solution (DMSO). Finally, the HOMO–LUMO energy levels were also constructed to study the electronic transition within the molecule by time-dependent TD-DFT method.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. S. Fustero, M. Sanchez-Rosello, P. Barrio, A. Simon-Fuentes, Chem. Rev. 111, 6984–7034 (2011)

    Article  CAS  Google Scholar 

  2. A.A. Bekhit, A. Hymete, A.A. Bekhit, A.D. Mamuye, H.Y. Aboul-Enein, Rev. Med. Chem. 10, 1014–1033 (2010)

    Article  CAS  Google Scholar 

  3. L. Nagarapu, J. Mateti, H.K. Gaikwad, R. Bantu, M. Sheeba, Rani, N.J. Prameela Subhashini. Bioorg. Med. Chem. Lett. 21, 4138–4140 (2011)

    Article  CAS  Google Scholar 

  4. F.F. Noe, L. Fowden, Nature 184, 69–70 (1959)

    Article  CAS  Google Scholar 

  5. S.L. Zhu, Y. Wu, C.-J. Liu, C.-J. Wei, J.-C. Tao, H.-M. Liu, Eur. J. Med. Chem. 65, 70–82 (2013)

    Article  CAS  Google Scholar 

  6. S. Viveka, Dinesha, L.N. Madhu, G.K. Nagaraja, Monatsh. Chem. 146, 1547–1555 (2015)

    Article  CAS  Google Scholar 

  7. A.M. Vijesh, A.M. Isloor, P. Shetty, S. Sundershan, H.K. Fun, Eur. J. Med. Chem. 62, 410–415 (2013)

    Article  CAS  Google Scholar 

  8. S. Mert, R. Kasımoğulları, T. İça, F. Çolak, A. Altun, S. Ok, Eur. J. Med. Chem. 78, 86–96 (2014)

    Article  CAS  Google Scholar 

  9. B. Çalışkan, A. Yılmaz, I. Evren, S. Menevşe, O. Uludag, E. Banoglu, Med. Chem. Res. 22, 782–793 (2013)

    Article  Google Scholar 

  10. T. Dey, J. Jacob, S. Sahu, M. Baidya, Pharmacologyonline 1, 908–916 (2011)

    Google Scholar 

  11. P. Khloya, P. Kumar, A. Mittal, N.K. Aggarwal, P.K. Sharma, Org. Med. Chem. Lett. 3, 9 (2013)

    Article  Google Scholar 

  12. Ş.C. Pirol, B. Çalışkan, İ. Durmaz, R. Atalay, E. Banoglu, Eur. J. Med. Chem. 87, 140–149 (2014)

    Article  Google Scholar 

  13. O. Bruno, C. Brullo, F. Bondavalli, S. Schenone, S. Spisani, M.S. Falzarano, K. Varani, E. Barocelli, V. Ballabeni, C. Giorgio, M. Tognolini, Bioorg. Med. Chem. 17, 3379–3387 (2009)

    Article  CAS  Google Scholar 

  14. L.-L. Xu, C.-J. Zheng, L.-P. Sun, J. Miao, H.-R. Piao, Eur. J. Med. Chem. 48, 174–178 (2012)

    Article  CAS  Google Scholar 

  15. S. Viveka, G. Vasantha, Dinesha, S. Naveen, N.K. Lokanath, G.K. Nagaraja, Mol. Cryst. Liq. Cryst. (Accepted May 2015)

  16. Y.-H. Luo, B.-W. Sun, Spectrochim. Acta Part A. 120, 381–388 (2014)

    Article  CAS  Google Scholar 

  17. S. Viveka, M. Prabhuswamy, Dinesha, N.K. Lokanath, G.K. Nagaraja, Mol. Cryst. Liq. Cryst. 593, 261–270 (2014)

    Article  CAS  Google Scholar 

  18. Bruker. SAINT PLUS, Bruker AXS Inc. Madison, Wisconsin, USA (2012)

  19. G. te Velde, F.M. Bickelhaupt, S.J.A. van Gisbergen, C.F. Guerra, E.J. Baerends, J.G. Snijders, T. Ziegler, J. Comput. Chem. 22, 931–967 (2001)

    Article  Google Scholar 

  20. GUI. SCM, Amsterdam, The Netherlands, http://www.scm.com (2014)

  21. J.P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 77, 3865–3868 (1996)

    Article  CAS  Google Scholar 

  22. G.M. Sheldrick, Acta Cryst. A64, 112–122 (2008)

    Article  Google Scholar 

  23. A.L. Spek, Acta. Cryst. A46, C34 (1990)

    Google Scholar 

  24. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P.A. Wood, J. Appl. Cryst. 41, 466–470 (2008)

    Article  CAS  Google Scholar 

  25. S. Viveka, Dinesha, P. Shama, G.K. Nagaraja, N. Deepa, M.Y. Sreenivasa, Res. Chem. Intermed. (2015) (Accepted)

  26. S. Viveka, Dinesha, P. Shama, G.K. Nagaraja, S. Ballav, S. Kerkar, Eur. J. Med. Chem. 101, 442–451 (2015)

    Article  CAS  Google Scholar 

  27. S. Viveka, Dinesha, S.S. Laxmeshwar, G.K. Nagaraja, Molbank. 3, M776 (2012)

    Article  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility. The authors gratefully acknowledge the DST-PURSE for the financial assistance. The authors thank Mangalore University for IR, DSC and TGA instrumental facilities. We are grateful to the Indian Institute of Science, Bangalore, for the NMR facility.

Author information

Authors and Affiliations

  1. Department of Studies in Chemistry, Mangalagangotri, Mangalore University, Konaje, 574199, India

    Shivapura Viveka,  Dinesha & Gundibasappa Karikannar Nagaraja

  2. Chemistry of Interfaces, Division of Chemical Engineering, Luleå University of Technology, 97187, Luleå, Sweden

    Gowda Vasantha

  3. Institution of Excellence, Vijnana Bhavana, Manasagangotri, University of Mysore, Mysore, 570006, India

    Shivalingegowda Naveen

  4. Department of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570006, India

    Neratur Krishnappagowda Lokanath

Authors
  1. Shivapura Viveka
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gowda Vasantha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dinesha
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shivalingegowda Naveen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Neratur Krishnappagowda Lokanath
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Gundibasappa Karikannar Nagaraja
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gundibasappa Karikannar Nagaraja.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Viveka, S., Vasantha, G., Dinesha et al. Structural, spectral, and theoretical investigations of 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid. Res Chem Intermed 42, 4497–4511 (2016). https://doi.org/10.1007/s11164-015-2292-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2292-y

Keywords

Search

Navigation