Skip to main content
SpringerLink
Log in

Electron diffraction and quantum-chemical studies of the molecular structure of 2-methylbenzenesulfochloride

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

Abstract

A combined electron diffraction and quantum-chemical (MP2/6-31G**) study of the molecular structure of 2-methylbenzenesulfochloride at 336(5) K was carried out. It was found that the gas phase contained only one conformer, C 1. The following structural parameters were obtained: r h1(C-H)av = 1.095(8) Å, r h1(C-C)Ph = 1.402(4) Å, r h1(CPh-Cmeth) = 1.507(13) Å, r h1(CPh-S) = 1.763(6) Å, r h1(S=O) = 1.418(4) Å, r h1(S-Cl) = 2.048(5) Å, ∠(H-C-H)meth/av = 107.3(96)°, ∠(Cl-S-O)av = 106.4(3)°, ∠CPh-S-Cl = 100.8(9), ∠O=S=O = 120.8(10)°. The CC-CS-S-Cl torsion angle that defines the position of the S-Cl bond relative to the plane of the benzene ring is 75.6(20)°. The B3LYP/6-311+G** calculated barriers of internal rotation of the methyl and sulfochloride groups are 1.2 kcal/mol and V 01 = 10.2 (V 02 = 4.1) kcal/mol, respectively.

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. Y. 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, No. 2, 208–216 (2000).

    Google Scholar 

  5. V. M. Petrov, V. N. Petrova, V. V. Kislov, et al., J. Struct. Chem., 41, No. 6, 939–947 (2000).

    Article  CAS  Google Scholar 

  6. V. N. Petrova, V. M. Petrov, G. V. Girichev, et al., ibid., 48, No. 4, 634–641 (2007).

    Article  CAS  Google Scholar 

  7. A. A. Potekhin (ed.), Properties of Organic Compounds. Handbook [in Russian], Khimiya, Leningrad (1984).

    Google Scholar 

  8. G. V. Girichev, S. A. Shlykov, and Yu. F. Revichev, Prib. Tekh. Eksp., No. 4, 167–169 (1986).

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

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

    Google Scholar 

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

    Article  Google Scholar 

  12. B. Andersen, H. M. Seip, T. G. Strand, and R. Stolevik, Acta Chem. Scand., 23, 322 (1969).

    Article  Google Scholar 

  13. A.-R. Campanelli, A. Domenicano, and F. Ramondo, J. Phys. Chem., A107, 6429 (2003).

    Google Scholar 

  14. 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 Engineering University, Russia

    V. N. Petrova, G. V. Girichev & A. V. Krasnov

  2. Ivanovo State University, Russia

    V. M. Petrov, A. V. Bardina & S. N. Ivanov

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

    H. Oberhammer

Authors
  1. V. M. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. N. Petrova
    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. A. V. Bardina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. N. Ivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. V. Krasnov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. V. Girichev.

Additional information

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

__________

Translated from Zhurnal Strukturnoi Khimii, Vol. 48, No. 6, pp. 1089–1096, November–December, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Petrov, V.M., Petrova, V.N., Girichev, G.V. et al. Electron diffraction and quantum-chemical studies of the molecular structure of 2-methylbenzenesulfochloride. J Struct Chem 48, 1022–1029 (2007). https://doi.org/10.1007/s10947-007-0166-x

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10947-007-0166-x

Keywords

Search

Navigation