Skip to main content
SpringerLink
Log in

Spectroscopic Studies of CDPy Molecule in Different Protic and Aprotic Solvents and Investigation of Antioxidant Property

  • Original Article
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The properties of 3-Cyano-4, 6-Dimethyl-2-Pyridone (CDPy) were analyzed to study the antioxidant behavior. The UV-Visible absorption and fluorescence properties of CDPy have been studied in two protic (water and methanol) and two aprotic (acetonitrile and dimethyl sulfoxide) solvents. Its antioxidant properties were compared with well known antioxidant ascorbic acid. This compound, CDPy was found to exhibits moderate antioxidant properties. The experimental results were reproduced by theoretical density functional methods, which helped to understand the experimental result better.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Dragovich PS, Prins TJ, Zhou R, Jhonson TO, Brown EL, Maldonado FC, Fuhrman SA, Zalman LS, Patick AK, Mathews DA, Hou X, Meador JW, Perre RA, Worland ST (2002) Structure-based design, synthesis and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. Part 7. Structure-activities and studies of bicyclic 2-pyridone containing peptidomimetics. Bioorg Med Chem Lett 12:733–738

    Article  CAS  Google Scholar 

  2. Cox RJ, O’hagan DJ (1991) Synthesis of isotopically labelled 3-amino-2-phenylpropionic acid and its role as a precursor in the biosynthesis of tenellin and tropic acid. Chem Soc Perkin Trans 1:2537

    Article  Google Scholar 

  3. Li Q, Mitscher LA, Shen LL (2000) The 2-Pyridone antibacterial agents: bacterial topoisomerase inhibitors. Med Res Rev 20:231–293

    Article  CAS  Google Scholar 

  4. Heo JN, Song YS, Kim BT (2005) Microwave-promoted synthesis of amino-substituted 2-pyridone derivatives via palladium-catalyzed amination reaction. Tetrahedron Lett 46:4621–4625

    Article  CAS  Google Scholar 

  5. Cetina M, Tranfic M, Sviben I, Jukic M (2010) Synthesis, X-ray and spectroscopic analysis of some pyridine derivatives. J Mol Struct 969:25–32

    Article  CAS  Google Scholar 

  6. Bridhkoti JP, Mishra H, Joshi HC, Pant S Photochemistry of 5-aminoquinoline in protic and aprotic solvents

  7. Raikar US, Renuka CG, Nadaf YF, Mulimani BG, Karguppikar AM, Soudagar MK (2006) Solvent effects on the absorption and fluorescence spectra of coumarins 6 and 7 molecules: determination of ground and excited state dipole moment. Spectrochim Acta A 65:673–677

    Article  CAS  Google Scholar 

  8. Dutt GB, Ghanty TK (2004) Fluorescence Anisotropy of 2,5,8,11-Tetra-tert-butylperylene and 2,5,10,13-Tetra-tert-butylterrylene in Alkanes and Alcohols. J Chem Phys 121:3625–3631

    Article  CAS  PubMed  Google Scholar 

  9. Singh R, Rai SK, Tiwari MK, Mishra A, Tewari AK, Mishra PC, Singh RK (2017) An excellent stable fluorescent probe: selective and sensitive detection of trace amounts of Hg+2 ions in natural source of water. Chem Phys Lett 676:39–45

    Article  CAS  Google Scholar 

  10. Ravishankara MN, Shrivastava N, Padh H, Rajani M (2002) Evaluation of antioxidant properties of root bark of Hemidesmus indicus. Phytomedicine 9:153–160

    Article  CAS  PubMed  Google Scholar 

  11. Anandjiwala S, Bagul MS, Parabia M, Rajani M (2008) Evaluation of free radical scavenging activity of an ayurvedic formulation, panchvalkala. Indian J Pharm Sci 70(1):31–35

    Article  PubMed  PubMed Central  Google Scholar 

  12. Zhao Y, Truhlar DG (2006) Application of two and three way chemometric methods in the study of acetylsalicylic acid and ascorbic acid mixtures using ultraviolet spectrophotometry. J Phys Chem A 110:5121–5129

    Article  CAS  PubMed  Google Scholar 

  13. Marenich AV, Cramer CJ, Truhlar DG (2009) Ground and excited state intramolecular proton transfer in salicylic acid: an Ab-initio electronic structure investigation. J Phys Chem B 113:6378–6396

    Article  CAS  PubMed  Google Scholar 

  14. Singh R, Tiwari MK, Gangopadhyay D, Mishra PC, Mishra H, Srivastava A, Singh RK (2018) Detection and monitoring of in vitro formation of salicylic acid from aspirin using fluorescence spectroscopic technique and DFT calculations. J Photochem Photobiol B Biol 189:292–297

    Article  CAS  Google Scholar 

  15. Singh R, Mishra VK, Singh HK, Sharma G, Koch B, Singh B, Singh RK (2018) Mg co-ordination with potential carcinogenic molecule acrylamide: spectroscopic, computational and cytotoxicity studies. J Mol Struct 1155:330–336

    Article  CAS  Google Scholar 

  16. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam MJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J (2009) Gaussian 09, revision B.01, Gaussian Inc., Wallingford, CT USA

  17. Dennington R, Keith T, Millam J (2009) GaussView, Version 5. Semichem. Inc, Shawnee

  18. Marcus RA (1964) Chemical and electrochemical electron-transfer theory. Annu Rev Phys Chem 15:155–196

    Article  CAS  Google Scholar 

  19. Marcus RA (1993) Electron transfer reactions in chemistry, theory and experiment. Rev Mod Phys 6:599

    Article  Google Scholar 

  20. Marcus RA (1997) Electron transfer reactions in chemistry, theory and experiment, pure Appl. Chem. 69:13–29

    CAS  Google Scholar 

  21. Nelsen SF, Blackstock SC, Kim Y (1987) Estimation of inner shell Marcus terms for amino nitrogen compounds by molecular orbital calculations. J Am Chem Soc 109:677–682

    Article  CAS  Google Scholar 

  22. Nelsen SF, Weaver MN, Luo Y, Pladziewicz JR, Ausman LK, Jentzsch TL, O’Konek JJ (2006) Estimation of electronic coupling for intermolecular electron transfer from cross-reaction data. J Phys Chem A 110:11665–11676

    Article  CAS  PubMed  Google Scholar 

  23. Tiwari MK, Mishra PC (2016) Anti-oxidant activity of 6-gingerol as a hydroxyl radical scavenger by hydrogen atom transfer, radical addition and electron transfer mechanisms. J Chem Sci 128:1199–1210

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Dr. Ranjana Singh is grateful for providing financial support in terms of CSIR Research Associate ship with file no 09/13 (0846)/2018-EMR-I dated 29/03/2019 by CSIR New Delhi, Govt. of India. I want to heartily acknowledge Late Prof. P. C. Mishra Sir for his excellent guidance during starting of the present work. Authors want to give due their sincere thanks to Dr. Sunil Rai to provide important chemicals during the measurements. Authors are also thankful to Biophysics Laboratory, Department of Physics, B. H. U. Varanasi, India to access the Edinburg FLS 900 fluorescence spectrophotometer under UPE scheme for PL measurement and UV-Visible absorption spectrometer.

Author information

Authors and Affiliations

  1. Department of Physics, Institute of Science, Banaras Hindu University, Varanasi, 221005, India

    Ranjana Singh & Ranjan K. Singh

  2. Department of Physics, Mahatma Gandhi Kashi Vidyapith, Varanasi, 221001, India

    Manish K. Tiwari

  3. Department of Botony, Institute of Science, Banaras Hindu University, Varanasi, 221005, India

    Jyoti Goutam

Authors
  1. Ranjana Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Manish K. Tiwari
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jyoti Goutam
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ranjan K. Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Ranjana Singh or Ranjan K. Singh.

Ethics declarations

Conflict of Interests

The authors declare no competing financial interest.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Singh, R., Tiwari, M.K., Goutam, J. et al. Spectroscopic Studies of CDPy Molecule in Different Protic and Aprotic Solvents and Investigation of Antioxidant Property. J Fluoresc 30, 1439–1446 (2020). https://doi.org/10.1007/s10895-020-02589-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-020-02589-w

Keywords

Search

Navigation