Skip to main content
SpringerLink
Log in

Synthesis, Characterization, Structure, Ab Initio and DFT Calculations of 2-Amino-N-(3-phenylprop-2-enylidene)aniline

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

New Schiff base compound 2-amino-N-(3-phenylprop-2-enylidene)aniline, 1, was prepared by condensation of cinnamaldehyde with o-phenylenediamine and characterized by elemental analyses, UV–Vis and FT-IR spectroscopy. The crystal structure of 1 was determined by X-ray crystallography from single-crystal data and displays a trans configuration about the C=N double bond. In the crystal structure of 1, the molecule is located on an inversion center, so that it is disordered around the center of central C–C bond. The results from both the experimental and theoretical calculations are compared in this paper.

Graphical Abstract

New Schiff base compound 2-amino-N-(3-phenylprop-2-enylidene)aniline, 1, was prepared by condensation of cinnamaldehyde with o-phenylenediamine and characterized by elemental analyses, UV-Vis and FT-IR spectroscopy. The crystals structure of 1 was determined by X-ray crystallography from single-crystal data and displays a trans configuration about the C=N double bond.

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

Similar content being viewed by others

References

  1. Khalaji AD, Weil M, Hadadzadeh H, Daryanavard M (2009) Inorg Chim Acta 362:4837–4842

    Article  Google Scholar 

  2. Morshedi M, Amirnasr M, Triki S, Khalaji AD (2009) Inorg Chim Acta 362:1637–1640

    Article  CAS  Google Scholar 

  3. Morshedi M, Amirnasr M, Slawin AMZ, Woollins JD, Khalaji AD (2009) Polyhedron 28:167–171

    Article  CAS  Google Scholar 

  4. Khalaji AD, Hadadzadeh H, Gotoh K, Ishida H (2009) Acta Cryst E65:m70

    CAS  Google Scholar 

  5. Khalaji AD, Fejfarova K, Dusek M (2009) Acta Cryst E65:o1773

    Google Scholar 

  6. Fejfarova K, khalaji AD, Dusek M (2009) Acta Cryst E65:o2288

    CAS  Google Scholar 

  7. Laye RH (2007) Inorg Chim Acta 360:439–447

    Article  CAS  Google Scholar 

  8. Khalaji AD, Aoki K, Amirnasr M (2007) J Coord Chem 60:201–206

    Article  CAS  Google Scholar 

  9. Amirnasr M, Khalaji AD, Falvello LR, Soler T (2006) Polyhedron 25:1967–1970

    Article  CAS  Google Scholar 

  10. Stilinovic V, Cincic D, Kaitner B (2008) Acta Chim Slov 55:874–879

    CAS  Google Scholar 

  11. Omar MM, Mohemed GG, Ibrahim AA (2009) Spectrochim Acta A73:358–369

    Google Scholar 

  12. Abdallah SM, Mohamed GG, Zayed MA, El-lah MSA (2009) Spectrochim Acta A73:833–840

    Google Scholar 

  13. Ispir E (2009) Dyes Pigments 82:13–19

    Article  CAS  Google Scholar 

  14. Nejati K, Rezvani Z, Massoumi B (2007) Dyes Pigments 75:653–657

    Article  CAS  Google Scholar 

  15. Karakas A, Unver H, Elmali AJ (2008) Mol Structu 877:152–157

    Article  CAS  Google Scholar 

  16. Karakas A, Elmali A, Unver H, Svoboda I (2005) Spectrochim Acta A61:2979–2987

    Google Scholar 

  17. Hadjoudis E, Rontoyianni A, Ambroziak K, Dziembowska T, Mavridis IM (2004) J Photochem Photobiol A162:521–530

    Article  Google Scholar 

  18. Hijji YF, Barare B, Kennedy AP, Butcher R (2009) Sens Actuators B136:297–302

    CAS  Google Scholar 

  19. Sheldrick GM (2008) Acta Cryst A64:112–122

    CAS  Google Scholar 

  20. Farrugia LJ (1997) J Appl Cryst 30:565

    Article  CAS  Google Scholar 

  21. Frisch MJ et al (1998) GAUSSIAN 98, Revision A.9. Gaussian Inc, Pittsburgh

    Google Scholar 

Download references

Acknowledgments

We acknowledge Golestan University (GU) for partial support of this work and Okayama University (OU) for X-ray analysis.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran

    Aliakbar Dehno Khalaji & Hossein Mighani

  2. Department of Chemistry, Faculty of Science, Okayama University, Okayama, 700-8530, Japan

    Kazuma Gotoh & Hiroyuki Ishida

Authors
  1. Aliakbar Dehno Khalaji
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hossein Mighani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kazuma Gotoh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hiroyuki Ishida
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aliakbar Dehno Khalaji.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khalaji, A.D., Mighani, H., Gotoh, K. et al. Synthesis, Characterization, Structure, Ab Initio and DFT Calculations of 2-Amino-N-(3-phenylprop-2-enylidene)aniline. J Chem Crystallogr 41, 1154–1157 (2011). https://doi.org/10.1007/s10870-011-0062-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-0062-2

Keywords

Search

Navigation