Skip to main content
SpringerLink
Log in

Conformational Analysis and Study of Hydrogen Bonding of Iodobicycloheptanyl-N′-(trifluoromethanesulfonyl) Acetimidamides

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Structure of iodobicycloheptanyl-N′-(trifluoromethanesulfonyl) acetimidamide epimers and its self-associates in crystal, solution and gas phase was studied by X-ray diffraction, IR spectroscopy and quantum chemistry methods. In an isolated molecule, the 2S,7R-enantiomer is energetically preferred, the structure of which is also realized in the crystal. According to X-ray diffraction analysis, in the crystal, (2S,7R)-N-(7-iodobicyclo[2.2.1]heptan-2-yl)-N′-(trifluoromethanesulfonyl) acetimidamide molecules are linked by intermolecular hydrogen bonds R–NH···O=S. However, according to the quantum-chemical calculations data, the Tf-NH···O=S type H-bonds turn out to be stronger by 3 kcal/mol when dimers are formed. The relative energy of formation of (2S,7S)-N-7-iodobicyclo[2.2.1]heptan-2-yl)-N′-(trifluoromethanesulfonyl) acetimidamide self-associates is ~10 kcal/mol.

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.
Scheme
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. Mondal, S. and Malakar, S., Tetrahedron, 2020, vol. 76, p. 131662. https://doi.org/10.1016/j.tet.2020.131662

    Article  CAS  Google Scholar 

  2. Ghiano, D.G., Recio-Balsells, A., Bortolotti, A., Defelipe, L.A., Turjanski, A., Morbidoni, H.R., and Labadie, G.R., Eur. J. Med. Chem., 2020, vol. 208, p. 112699. https://doi.org/10.1016/j.ejmech.2020.112699

    Article  CAS  PubMed  Google Scholar 

  3. Grib, I., Berredjem, M., Otmane Rachedi, K., Djouad, S.-E., Bouacida, S., Bahadi, R., Ouk, T.-S., Kadrif, M., Ben Hadda, T., and Belhani, B., J. Mol. Str., 2020, vol. 1217, p. 128423. https://doi.org/10.1016/j.molstruc.2020.128423

    Article  CAS  Google Scholar 

  4. Mironova, E.V., Lodochnikova, O.A., Krivolapov, D.B., Veremeichik, Ya.V., Plemenkov, V.V., and Litvinov, I.A., J. Struct. Chem., 2014, vol. 55, no. 3, p. 539. https://doi.org/10.1134/S0022476614030238

    Article  CAS  Google Scholar 

  5. Zlenko, E.T., Kas’yan, L.I., Mamchur, V.I., Kas’yan, A.O., Prid’ma, S.A., Pal’chikov, V.A., and Karat, L.D., Zh. Org. Farm. Khim., 2009, vol. 7, no. 1(25), p. 64.

    CAS  Google Scholar 

  6. Gorpinchenko, V.A., Yatsynich, E.A., Petrov, D.V., Karachurina, L.T., Hisamutdinova, R.Yu., Baschenko, N.Zh., Dokichev, V.A., Tomilov, Yu.V., Yunusov, M.S., and Nefedov, O.M., Pharm. Chem. J., 2005, vol. 39, no. 6, p. 289. https://doi.org/10.1007/s11094-005-0135-7

    Article  CAS  Google Scholar 

  7. Moskalik, M.Yu., Shainyan, B.A., Ushakov, I.A., Sterkhova, I.V., and Astakhova, V.V., Tetrahedron, 2020, vol. 76, p. 131018. https://doi.org/10.1016/j.tet.2020.131018

    Article  CAS  Google Scholar 

  8. Sterkhova, I.V., Moskalik, M.Yu., and Shainyan, B.A., Russ. J. Org. Chem., 2013, vol. 49, no. 11, p. 1594. https://doi.org/10.1134/S1070428013110055

    Article  CAS  Google Scholar 

  9. Sterkhova, I.V., Moskalik, M.Yu., and Shainyan, B.A., Russ. J. Org. Chem., 2014, vol. 50, no. 3, p. 337. https://doi.org/10.1134/S1070428014030051

    Article  CAS  Google Scholar 

  10. Sterkhova, I.V., Nikonov, A.Yu., Lazarev, I.M., Moskalik, M.Yu., and Lazareva, N.F., Russ. J. Gen. Chem., 2015, vol. 85, no. 7, p. 1661. https://doi.org/10.1134/S1070363215070154

    Article  CAS  Google Scholar 

  11. Shainyan, B.A., Meshcheryakov, V.I., and Sterkhova, I.V., Tetrahedron, 2015, vol. 71, p. 7906. https://doi.org/10.1016/j.tet.2015.08.008

    Article  CAS  Google Scholar 

  12. Bartashevich, E.V. and Tsirelson, V.G., Russ. Chem. Rev., 2014, vol. 83, no. 12, p. 1181. https://doi.org/10.1070/RCR4440

    Article  CAS  Google Scholar 

  13. Johnson, R.D.III., NIST Computational Chemistry Comparison and Benchmark Database, Precomputed Vibrational Scaling Factors. http://cccbdb.nist.gov/vibscalejust.asp

  14. Weinhold, F. and Landis, C.R., Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective, Cambridge: University Press, 2005.

  15. Glendening, E.D., Reed, A.E., Carpenter, J.E., and Weinhold, F., NBO Version 3.1, Gaussian, Inc., Pittsburgh, PA, CT, 2003.

  16. Fernandez, L.E., Ben Altabef, A., Fantoni, A.C., and Varetti, E.L., Spectrochim. Acta (A), 1997, vol. 53, p. 189. https://doi.org/10.1016/S1386-1425(97)83025-9

    Article  Google Scholar 

  17. Soldatenko, A.S., Sterkhova, I.V., and Lazareva, N.F., J. Organomet. Chem., 2019, vol. 903, p. 120997. https://doi.org/10.1016/j.jorganchem.2019.120997

    Article  CAS  Google Scholar 

  18. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A.Jr., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., and Pople, J.A., GAUSSIAN 09, Revision, A.01, Gaussian Inc., Wallingford CT, 2009.

  19. Sheldrick, G.M., Acta Crystallogr. (D), 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The studies were carried out using the equipment of the material and technical base of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033, Irkutsk, Russia

    I. V. Sterkhova, T. E. Fedorova & M. Yu. Moskalik

Authors
  1. I. V. Sterkhova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. E. Fedorova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Yu. Moskalik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Sterkhova.

Ethics declarations

No conflict of interest was declared by the authors.

Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 5, pp. 720–727 https://doi.org/10.31857/S0044460X21050085.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sterkhova, I.V., Fedorova, T.E. & Moskalik, M.Y. Conformational Analysis and Study of Hydrogen Bonding of Iodobicycloheptanyl-N′-(trifluoromethanesulfonyl) Acetimidamides. Russ J Gen Chem 91, 807–813 (2021). https://doi.org/10.1134/S107036322105008X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107036322105008X

Keywords:

Search

Navigation