Skip to main content
SpringerLink
Log in

Investigation of the Molecular Structure of (E)-2-Bromo-6-[(4-bromo-2-methylphenylimino)methyl]-4-chlorophenol

  • STRUCTURE OF ORGANIC COMPOUNDS
  • Published:
Crystallography Reports Aims and scope Submit manuscript

Abstract

In this study, the molecular structure of (E)-2-bromo-6-[(4-bromo-2-methylphenylimino)methyl]-4-chlorophenol has been investigated using crystallographic (XRD), spectroscopic (UV-vis, NMR), and computational (DFT, HOMA) methods. The refinement parameters in XRD study supports the preference of phenol-imine form by the compound in solid state. The analysis of HOMA indices indicates that C1/C6 ring (tautomeric ring) deviates slightly from the aromaticity while the C8/C13 ring preserves its aromaticity in solid state. For the solvent-media dependence of the tautomerism, UV-vis and NMR spectra of the compound were investigated. It is found that the compound prefers only phenol-imine form in solvent media as in the case of solid state.

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.

Similar content being viewed by others

REFERENCES

  1. E. Hadjoudis, M. Vitterakis, and I. Moustakali-Mavridis, Tetrahedron 43, 1345 (1987).

    Article  Google Scholar 

  2. I. Moustakali-Mavridis, E. Hadjoudis, and A. Mavridis, Acta Crystallogr., Sect. B 34, 3709 (1978).

    Article  Google Scholar 

  3. E. Hadjoudis, in Photochromism: Molecules and Systems, Ed. by H. Dürr and Bouas-Laurent (Elsevier, Amsterdam, 1990), p. 685.

  4. K. Amimoto and T. Kawato, J. Photochem. Photobiol. C 6, 207 (2005).

    Article  Google Scholar 

  5. F. Milia, E. Hadjoudis, and J. Seliger, J. Mol. Struct. 177, 191 (1988).

    Article  ADS  Google Scholar 

  6. M. J. Frisch, G. W. Trucks, H. B. Schlegel, et. al., Gaussian 03, Revision E.01 (Gaussian Inc., Wallingford CT, 2004).

  7. R. Dennington, T. Keith, and J. Millam, GaussView, Version 4.1.2. (Semichem Inc., Shawnee Mission, 2007).

    Google Scholar 

  8. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, et al., J. Phys. Chem. 98, 11623 (1994).

    Article  Google Scholar 

  9. P. C. Hariharan and J. A. Pople, Theor. Chim. Acta (Berlin) 28, 213 (1973).

    Article  Google Scholar 

  10. G. M. Sheldrick, Acta Crystallogr. A 71, 3 (2015).

    Article  Google Scholar 

  11. G. M. Sheldrick, Acta Crystallogr., C 71, 3 (2015).

    Article  Google Scholar 

  12. L. J. Farrugia, J. Appl. Crystallogr. 45, 849 (2012).

    Article  Google Scholar 

  13. L. J. Farrugia, J. Appl. Crystallogr. 30, 565 (1997).

    Article  Google Scholar 

  14. S. Kevran, A. Elmali, and Y. Elerman, Acta Crystallogr. C 52, 3256 (1996).

    Article  Google Scholar 

  15. A. Elmali, Y. Elerman, I. Svoboda, et al., Acta Crystallogr. C 54, 974 (1998).

    Article  Google Scholar 

  16. Z. Popović, G. Pavlović, D. Matković-Čalogović, et al., J. Mol. Struct. 615, 23 (2002).

    Article  ADS  Google Scholar 

  17. T. M. Krygowski, J. Chem. Inf. Comput. Sci. 33, 70 (1993).

    Article  Google Scholar 

  18. T. M. Krygowski, J. E. Zachara, and R. Moszynski, J. Chem. Inf. Model. 45, 1837 (2005).

    Article  Google Scholar 

  19. K. A. Abbas, S. R. Salman, S. M. Kana’n, et al., Can. J. Appl. Spectrosc. 41, 119 (1996).

    Google Scholar 

  20. T. Dziembowska, E. Jagodzińska, Z. Rozwadowski, et al., J. Mol. Struct. 598, 229 (2001).

    Article  ADS  Google Scholar 

Download references

ACKNOWLEDGMENTS

This work was supported by Sinop University Scientific Research Coordination Unit. Project no. FEF-1901-13-07. The authors acknowledge to Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.

Author information

Authors and Affiliations

  1. Samsun University, Department of Aircraft Maintenance, Faculty of Aeronautics and Astronautics, Samsun, Turkey

    G. Kaştaş

  2. Sinop University, Department of Chemistry, Faculty of Arts and Sciences, Sinop, Turkey

    Ç. Albayrak Kaştaş

  3. Sinop University, Department of Physics, Faculty of Arts and Sciences, Sinop, Turkey

    C. C. Ersanlı

  4. Sinop University, Department of Science Education, Faculty of Education, Sinop, Turkey

    B. Koşar Kırca

Authors
  1. G. Kaştaş
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ç. Albayrak Kaştaş
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. C. C. Ersanlı
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. B. Koşar Kırca
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. Kaştaş.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaştaş, G., Kaştaş, Ç.A., Ersanlı, C.C. et al. Investigation of the Molecular Structure of (E)-2-Bromo-6-[(4-bromo-2-methylphenylimino)methyl]-4-chlorophenol. Crystallogr. Rep. 65, 463–467 (2020). https://doi.org/10.1134/S1063774520030153

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1063774520030153

Search

Navigation