Skip to main content
SpringerLink
Log in

Electron diffraction and quantum-chemical studies of the conformational properties of the 1,3-benzenedisulfochloride molecule

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

A combined electron diffraction (T = 394(5) K) and quantum-chemical (MP2/6-31G**) study has been performed to investigate the molecular structure of 1,3-benzenedisulfochloride (1,3-BDSC). The 1,3-BDSC molecule was found to exist as the trans (I) and cis (II) stable conformers where the planes containing S-Cl bonds are perpendicular to the plane of the benzene ring. The energy of conformer I is 0.13 kJ/mol lower than that of conformer II. The mutual effect of the sulfochloride groups was found to be absent, which is evident from the coincident bond lengths and angles in the two conformers. The main structural parameters of the conformers are r h1(C-H)av = 1.103(4) Å, r h1(C-C)av = 1.401(3) Å, r h1(C-S) = 1.767(4) Å, r h1(S=O) = 1.422(3) Å, r h1(S-Cl) = 2.048(4) Å, ∠Cl-S-O = 106.6(2)°, ∠C-S-Cl = 100.4(5)°, ∠ O-S-O = 123.2(5)°.

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. V. M. Petrov, V. N. Petrova, V. V. Kislov, et al., J. Struct. Chem., 40, No. 4, 533–540 (1999).

    Article  CAS  Google Scholar 

  2. V. V. Kislov, V. M. Petrov, S. Yu. Noskov, et al., Internet J. Chem., 2, art. 9 (1999).

  3. V. V. Kislov, S. N. Ivanov, and V. M. Petrov, J. Struct. Chem., 41, No. 5, 749–756 (2000).

    Article  CAS  Google Scholar 

  4. V. V. Kislov and S. N. Ivanov, Zh. Obshch. Khim., 70, issue 2, 208–216 (2000).

    Google Scholar 

  5. V. M. Petrov, V. N. Petrova, V. V. Kislov, et al., J. Struct. Chem., 41, No. 6, 939–647 (2000).

    Article  CAS  Google Scholar 

  6. L. M. Litvinenko, V. A. Savelova, T. N. Solomoichenko, and V. G. Zaslavskii, Structure and Reactivity of Organic Compounds and Mechanisms of Reactions [in Russian], Naukova Dumka, Kiev (1980), pp. 3–68.

    Google Scholar 

  7. A. R. Haughton, R. M. Laird, and M. J. Spence, J. Chem. Soc., Perkin Trans. II, No. 6, 637–643 (1975).

    Google Scholar 

  8. K. W. Buller, Heat-and Temperature-Resistant Polymers [in Russian], Ya. S. Vygodskii (ed.), Khimiya, Moscow (1984), pp. 248–251.

    Google Scholar 

  9. Yu. A. Moskvichev, V. A. Sapunov, and G. S. Mironov, Zh. Prikl. Khim., 53, issue 7, 619–624 (1980).

    Google Scholar 

  10. Yu. A. Moskvichev, G. N. Timoshenko, A. K. Grigorichev, et al., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 39, issue 3, 82–84 (1996).

    CAS  Google Scholar 

  11. A. V. Tarasov, “Syntheses and chemical transformations of aromatic mono-and dichlorides of sulfo and sulfocarboxylic acids,” Chemical Sciences Doctoral Dissertation, Yaroslavl State Technical University, Yaroslavl (2003).

    Google Scholar 

  12. G. V. Girichev, A. N. Utkin, and Yu. F. Revichev, Prib. Tekh. Eksp., No. 2, 457–459 (1984).

  13. G. V. Girichev, S. A. Shlykov, and Yu. F. Revichev, ibid., No. 4, 167–169 (1986).

  14. C. Sjuter, Chemistry of Organic Connections of Sulfur [Russian translation], Vol. 2, INLIT, Moscow (1951).

    Google Scholar 

  15. E. G. Girichev, A. V. Zakharov, G. V. Girichev, and M. I. Bazanov, Izv. Vyssh. Uchebn. Zaved., Tekstil. Prom-st, No. 2, 142–146 (2000).

  16. M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 03, Revision B. 04, Gaussian, Inc., Pittsburgh, PA (2003).

    Google Scholar 

  17. V. A. Sipachev, J. Mol. Struct., 567/568, 67 (2001); V. A. Sipachev, ibid., 121, 143 (1985); V. A. Sipachev, in Advances in Molecular Structure Research, I. Hargittai and M. Hargittai (eds.), Vol. 5, JAI Press, New York (1999), p. 263.

    Article  Google Scholar 

  18. B. Andersen, H. M. Seip, T. G. Strand, and R. Stolevik, Acta Chem. Scand., 23, 3224 (1969).

    Article  CAS  Google Scholar 

  19. W. C. Hamilton, Acta Crystallogr., 18, 502 (1965).

    Article  CAS  Google Scholar 

  20. J. Brunvoll and I. Hargittai, J. Mol. Struct., 30, 361–378 (1976).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ivanovo State Chemical and Engineering University, Ivanovo

    V. N. Petrova & G. V. Girichev

  2. Ivanovo State University, Ivanovo

    V. M. Petrov & S. N. Ivanov

  3. Institute of Physical and Theoretical Chemistry, Tubingen University, Germany

    H. Oberhammer

Authors
  1. V. N. Petrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. M. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. V. Girichev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. H. Oberhammer
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. N. Ivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. V. Girichev.

Additional information

__________

Translated from Zhurnal Strukturnoi Khimii, Vol. 48, No. 4, pp. 686–692, July–August, 2007.

Original Russian Text Copyright © 2007 by V. N. Petrova, V. M. Petrov, G. V. Girichev, H. Oberhammer, and S. N. Ivanov

Rights and permissions

Reprints and permissions

About this article

Cite this article

Petrova, V.N., Petrov, V.M., Girichev, G.V. et al. Electron diffraction and quantum-chemical studies of the conformational properties of the 1,3-benzenedisulfochloride molecule. J Struct Chem 48, 634–641 (2007). https://doi.org/10.1007/s10947-007-0096-7

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10947-007-0096-7

Keywords

Search

Navigation