Skip to main content
SpringerLink
Log in

Crystal structure and linear-dichroic infrared (IR-LD) spectral analysis of N,N′-diethyl-4-vinylbenzamidinium squarate

  • Original Paper
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The synthesis and crystal structure of N,N′-diethyl-4-vinylbenzamidinium squarate (I) (C15H19N2O2) are reported. The squarate dianion (Sq2−) and (E,Z)-configured amidinium groups are linked through two intermolecular N···O hydrogen bonds with distances of 2.725 Å for E and 2.731 Å for the Z configurated amidinium parts, thus forming an infinite three-dimensional network. The torsion angle between phenylene ring and amidinium group is 66.1(2)° and the analogous one between the first fragment and the vinyl group 9.6(8)°. The IR-characteristic band assignment both in solution and in solid state has been carried out by means of non- and linear polarized IR- spectral analysis.

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 I
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme II

Similar content being viewed by others

Reference

  1. Kolev T, Spiteller M, Sheldrick WS, Mayer-Figge H Acta Crystallogr E (in preparation)

  2. Kolev T, Spiteller M, Sheldrick WS, Mayer-Figge H Acta Crystallogr E (in preparation)

  3. Wolff JJ, Wortmann R (1999) Organic materials for Second-Order Non-Linear optics. Adv Phys Org Chem 32:121

    Article  CAS  Google Scholar 

  4. Chemla D, Zyss J (1987) In: Chemla D, Zyss J (eds) Nonlinear optical properties of organic molecules and crystals, vol 1. Academic Press, New York, pp 23–187

  5. Nalwa HS, Watanabe T, Miyata S (1997) In: Nalwa HS, Miyata S (eds) Nonlinear optics of organic molecules and polymers. CRC Press, Boca Raton, pp 89–329

  6. Guilford WJ, Shaw KJ, Dallas JL, Koovakkat S, Lee W, Liang A, Light DR, McCarrick MA, Whitlow, M, Ye B, Morrissey MM (1999) J Med Chem 42:5415

    Article  CAS  Google Scholar 

  7. Tinant B, Dupont-Fenfau J, Declercq J-P, Podlaha J, Exner O (1989) Collect Czech Chem Commun 54:3245

    Article  CAS  Google Scholar 

  8. Alcock NW, Blacker NC, Errington W, Wallbridge MGH, Barker J (1994) Acta Crystallogr, Sect C 50:456

    Article  Google Scholar 

  9. Barker J, Errington W, Wallbridge MGH (1999) Acta Crystallogr, Sect C 55:1583

    Article  Google Scholar 

  10. Hartmann S, Weckert E, Frahm AW, McNally JJ,Youngman MA, Lovenberg TW, Nepomuceno DH, Wilson SJ (1999) Acta Crystallogr, Sect C 55:806

    Google Scholar 

  11. Peters L, Fröhlich R, Boyd ASF, Kraft AJ (2001) Org Chem 66:3291

    Article  CAS  Google Scholar 

  12. Wulff G, Schönfeld R (1998) Adv Mater 10:957

    Article  CAS  Google Scholar 

  13. Sheldrick GM (1995) SHELXTL, Release 5.03 for Siemens R3 crystallographic research system. Siemens Analytical X-Ray Instruments, Inc., Madison, USA

    Google Scholar 

  14. Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Goettingen, Germany

    Google Scholar 

  15. Ivanova BB, Arnaudov MG, Bontchev PR (2004) Spectrochim Acta 60A:855

    CAS  Google Scholar 

  16. Ivanova BB (2006) Spectrochim Acta 64A:931

    CAS  Google Scholar 

  17. Michl J, Thulstrup EW (1986) Spectroscopy with Polarized Light. Solute alignment by photoselection, in liquid crystals, polymers, and membranes. VCH Publishers, NY

    Google Scholar 

  18. Thulstrup EW, Eggers JH (1996) Chem Phys Lett 1:690

    Article  Google Scholar 

  19. Jordanov B, Schrader B (1995) J Mol Struct 347:389

    Article  CAS  Google Scholar 

  20. Jordanov B, Nentchovska R, Schrader B (1993) J Mol Struct 297:2922

    Article  Google Scholar 

  21. Ivanova BB, Tsalev DL, Arnaudov MG (2006) Talanta 69:822

    Article  CAS  Google Scholar 

  22. Ivanova BB, Simeonov VD, Arnaudov MG, Tsalev DL (2006) Spectrochim Acta Part A in press

  23. Kraft A, Peters L, Powell H (2002) Tetrahedron 28:3499

    Article  Google Scholar 

  24. Torii H, Tasumi M (1995) J Mol Struct Theochem 334:15

    Google Scholar 

  25. Wagner G, Garbe Ch, Richter P (1975) Pharmazie 30:444

    CAS  Google Scholar 

  26. Stamboliyska BA, Kolev TM (2005) Bulg Chem Commun 37:295

    CAS  Google Scholar 

Download references

Acknowledgements

T.K. and M.S. wish to thank the DAAD for a grant within the priority program “Stability Pact South-Eastern Europe,” the Alexander von Humboldt Foundation and the Bulgarian National Fund for Research, Grant X-1213.

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. build. 9, 1113, Sofia, Bulgaria

    Ts. Kolev

  2. Department of Analytical Chemistry, Sofia University “St. Kl. Ohridsky,” Faculty of Chemistry, 1164, Sofia, Bulgaria

    B. B. Koleva

  3. Institut für Umweltforschung, University at Dortmund, Otto-Hahn-Strasse 6, 44221, Dortmund, Germany

    M. Emgenbroich & M. Spiteller

  4. Lehrstuhl für Analytische Chemie, Ruhr-Universityat Bochum, University Satsstrasse 150, 44780, Bochum, Germany

    W. S. Sheldrick & H. Mayer-Figge

Authors
  1. Ts. Kolev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. B. Koleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Emgenbroich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Spiteller
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. W. S. Sheldrick
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. H. Mayer-Figge
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ts. Kolev.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kolev, T., Koleva, B.B., Emgenbroich, M. et al. Crystal structure and linear-dichroic infrared (IR-LD) spectral analysis of N,N′-diethyl-4-vinylbenzamidinium squarate. Struct Chem 17, 631–637 (2006). https://doi.org/10.1007/s11224-006-9110-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-006-9110-5

Keywords

Search

Navigation