Skip to main content
SpringerLink
Log in

Synthesis and structural study on (1E,2E,1′E,2′E)-3,3′-bis[(4-bromophenyl)-3,3′-(4-methy-1,2-phenylene diimine)] acetaldehyde dioxime: A combined experimental and theoretical study

  • Spectroscopy of Atoms and Molecules
  • Published:
Optics and Spectroscopy Aims and scope Submit manuscript

Abstract

Tetradentate (1E,2E,1′E,2′E)-3,3′-bis[(4-bromophenyl)-3,3′-(4-methy-1,2-phenylene diimine)] acetaldehyde dioxime which possess N4 donor sets derived from the condensation of isonitroso-p-bromoacetophenone and 3,4-diaminotoluene are synthesized and characterized. The characterization of tetradentate Schiff base ligand has been deduced from LC-MS, FTIR, 13C and 1H NMR spectra and elemental analysis. Furthermore, the molecular geometry, infrared and NMR spectra of the title molecule in the ground state have been calculated by using the quantum chemical computational methods such as density functional theory (DFT) and ab initio Hartree-Fock (HF) methods with the 6–31G(d) and 6–311G(d) basis sets. The computed bond lengths and bond angles by using the both methods show the good agreement with each other. Moreover, the vibrational frequencies have been calculated and the scaled values have been compared with the experimental FTIR spectroscopic data. Assignments of the vibrational modes are made on the basis of potential energy distribution (PED) calculated from by using VEDA program. The correlations between the observed and calculated frequencies are in good agreement with each other as well as the correlation of the NMR data.

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

Similar content being viewed by others

References

  1. G. H. Jeffery, J. Bassett, J. Mendham, and R. C. Denny, Vogel’s Textbook of Quantitative Chemical Analysis, 5th ed. (Addison Westley Longman Ltd., England, 1989).

    Google Scholar 

  2. V. Y. Kukushkin, D. Tudela, and A. J. L. Pombeiro, Coord. Chem. Rev. 156, 333 (1996).

    Article  Google Scholar 

  3. V. Y. Kukushkin and A. J. L. Pombeiro, Coord. Chem. Rev. 181, 147 (1999).

    Article  Google Scholar 

  4. P. Chaudhuri, Coord. Chem. Rev. 243, 143 (2003).

    Article  Google Scholar 

  5. D. Maity, S. Chattopadhyay, A. Ghosh, G. B. Drew Michael, and G. Mukhopadhyay, Inorg. Chim. Acta 365, 25 (2011).

    Article  Google Scholar 

  6. D. Maity, P. Mukherjee, A. Ghosh, G. B. Drew Michael, and G. Mukhopadhyay, Inorg. Chim. Acta 361, 1515 (2008).

    Article  Google Scholar 

  7. D. Maity, S. Chattopadhyay, A. Ghosh, G. B. Drew Michael, and G. Mukhopadhyay, Polyhedron 28, 812 (2009).

    Article  Google Scholar 

  8. J. P. Costes, F. Dahan, A. Dupuis, and J. P. Laurent, J. Chem. Soc. Dalton Trans., 1307 (1998).

    Google Scholar 

  9. S. Ganguly, S. Karmakar, C. K. Pal, and A. Chakravorty, Inorg. Chem. 38, 5984 (1999).

    Article  Google Scholar 

  10. N. Chitrapriya, V. Mahalingam, M. Zeller, H. Lee, and K. Natarajan, J. Mol. Struc. 984, 30 (2010).

    Article  ADS  Google Scholar 

  11. H. Sahebalzamani, S. Ghammamy, M. Kheyrollah, and F. Salimi, Der Chemica Sinica 1, 67 (2010).

    Google Scholar 

  12. U. Casellato, P. A. Vigato, and M. Vidali, Coord. Chem. Rev. 23, 31 (1977).

    Article  Google Scholar 

  13. O. Cecilia Rodriguez de Barbarin, Neil A. Bailey, David E. Fenton, and Qing-Yu He, J. Chem. Soc., Dalton Trans., 161 (1997).

    Google Scholar 

  14. H. Miyasaka, H. I. N. Matsumoto, N. Re, R. Crescenzi, and C. Floriani, Inorg. Chem. 387, 255 (1998).

    Article  Google Scholar 

  15. B. Dede, F. Karipcin, and M. Cengiz, J. Hazard. Mater. 163, 1148 (2009).

    Article  Google Scholar 

  16. V. Krishnakumar, R. J. Xavier, and T. Chithambarathanu, Spectrochim. Acta, Part A 62, 931 (2005).

    Article  ADS  Google Scholar 

  17. H. Chermette, Coordination Chem. Rev. 178–180, 699 (1998).

    Article  Google Scholar 

  18. C. Corminboeuf, F. Tran, and J. Weber, J. Mol. Struct.: Theochem 672, 1 (2006).

    Article  Google Scholar 

  19. R. A. Friesner, R. B. Murphy, M. D. Beachy, M. N. Ringnalda, W. T. Pollard, B. D. Dunietz, and Y. Coa, J. Phys. Chem. A 103(13), 1913 (1999).

    Article  Google Scholar 

  20. P. Wojciechowski, W. Zierkiewicz, D. Michalska, and P. Hobza, J. Chem. Phys. 118, 10900 (2003).

    Article  ADS  Google Scholar 

  21. M. Karabacak, E. Sahin, M. Cinar, I. Erol, and M. Kurt, J. Mol. Struct. 886, 148 (2008).

    Article  ADS  Google Scholar 

  22. X. Xuan, J. Wang, Y. Zhao, and J. Zhu, J. Raman Spectrosc. 38, 865 (2007).

    Article  ADS  Google Scholar 

  23. M. Karabacak, A. Coruh, and M. Kurt, J. Mol. Struct. 892, 125 (2008).

    Article  ADS  Google Scholar 

  24. N. Sundaraganesen, C. Meganathan, B. D. Joshua, P. Mani, and A. Jayaprakash, Spectrochim. Acta Part A 71, 1134 (2008).

    Article  ADS  Google Scholar 

  25. N. Sundaraganesen, C. Meganathan, and B. D. Joshua, Spectrochim. Acta, Part A 69, 871 (2008).

    Article  ADS  Google Scholar 

  26. X. Xuan and C. Zhai, Spectrochim. Acta A 79, 1663 (2011).

    Article  ADS  Google Scholar 

  27. M. R. Anoop, P. S. Binil, S. Suma, M. R. Sudarsnakumar, S. Mary Y. H. T. Vaghese, and C. Yohannan Pnicker, J. Mol. Struct. 969, 48 (2010).

    Article  ADS  Google Scholar 

  28. A. Atac, M. Karabacak, C. Karaca, and E. Köse, Spectrochim. Acta A 85, 145 (2012).

    Article  ADS  Google Scholar 

  29. M. Karabacak, Z. Cinar, M. Kurt, S. Sudha, and N. Sundaraganesan, Spectrochim. Acta A 85, 179 (2012).

    Article  ADS  Google Scholar 

  30. P. B. Nagabalasubramanian, M. Karabacak, and S. Periandy, Spectrochim. Acta A. 85, 43 (2012).

    Article  ADS  Google Scholar 

  31. M. Kurt, T. R. Sertbakan, M. Ozduran, and M. Karabacak, J. Mol. Struct. 921, 178 (2009).

    Article  ADS  Google Scholar 

  32. J. Baker, A. A. Jarzecki, and P. Pulay, J. Phys. Chem. A 102, 1412 (1998).

    Article  Google Scholar 

  33. J. Casanovas, A. M. Namba, S. Leon, G. L. B. Aquino, D. V. J. da Silva, and C. Aleman, J. Org. Chem. 66, 3775 (2001).

    Article  Google Scholar 

  34. I. Masud, Nippon Kagaku Zasshi 82, 120 (1961).

    Article  Google Scholar 

  35. A. Dornow and H. Theidel, Chemische Berichte 88, 1267 (1955).

    Article  Google Scholar 

  36. J. J. Norman, R. M. Heggie, and J. B. Larose, Can. J. Chem. 40, 1547 (1962).

    Article  Google Scholar 

  37. J. V. Burakevich, A. M. Lore, and G. P. Volpp, J. Org. Chem. 36, 1 (1971).

    Article  Google Scholar 

  38. F. Karipcin, S Ilican, Y. Çağlar, M Çağlar, B. Dede, and Y. Şahin, J. Organomet. Chem. 692 (2007)

  39. K. Serbest, S. Karaböcek, İ. Değirmencioğlu, S. Güner, and F. Kormali, Transit. Metal Chem. 26, 375 (2001).

    Article  Google Scholar 

  40. B. Dede, İ. Özmen, and F. Karipcin, Polyhedron 28, 3967 (2009).

    Article  Google Scholar 

  41. S. Karaböcek, N. Karaböcek, and A. Armutcu, Transit Metal Chem. 31, 459 (2006).

    Article  Google Scholar 

  42. N. Sundaraganesan, S. Ilakiamani, B. Anand, H. Saleem, and B. D. Joshua, Spectrochim. Acta, Part A 64, 586 (2006).

    Article  ADS  Google Scholar 

  43. J. B. Foresman and A. E. Frisch, Exploring Chemistry with Electronic Structure Methods (Gaussian Inc., 1996).

    Google Scholar 

  44. M. J. Frisch et al., Gaussian 09, Revision A.1 (Gaussian, Inc., Wallingford CT, 2009).

    Google Scholar 

  45. M. H. Jamroz, Vibrational Energy Distribution Analysis: VEDA 4 Program (Warsaw, 2004).

    Google Scholar 

  46. A. P. Scott and L. Radon, J. Phys. Chem. 100, 16502 (1996).

    Article  Google Scholar 

  47. M. K. Saha, S. Sen, T. Gupta, and S. Mitra, Transition Met. Chem. 23, 635 (1998).

    Article  Google Scholar 

  48. B. Dede, F. Karipcin, and M. Cengiz, J. Chem. Sci. 121, 163 (2009).

    Article  Google Scholar 

  49. M. Mirkovic, D. Jankovic, S. Vranjes-Durica, M. Radovic, D. Stankovic, D. Mijin, and N. Nikolic, Appl. Organomet. Chem. 26, 347 (2012).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Pamukkale University, Kinikli, 20017, Denizli, Turkey

    T. Topal & E. Karapınar

  2. Department of Physics, Pamukkale University, Kinikli, 20017, Denizli, Turkey

    H. H. Kart & P. Tunay Taşlı

Authors
  1. T. Topal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. H. Kart
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. Tunay Taşlı
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. Karapınar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to P. Tunay Taşlı.

Additional information

The article is published in the original.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Topal, T., Kart, H.H., Tunay Taşlı, P. et al. Synthesis and structural study on (1E,2E,1′E,2′E)-3,3′-bis[(4-bromophenyl)-3,3′-(4-methy-1,2-phenylene diimine)] acetaldehyde dioxime: A combined experimental and theoretical study. Opt. Spectrosc. 118, 865–881 (2015). https://doi.org/10.1134/S0030400X15060223

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0030400X15060223

Keywords

Search

Navigation