Skip to main content
SpringerLink
Log in

N-nitroimidoyl chlorides: synthesis and structure

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new method was developed for the synthesis of N-nitroimidoyl chlorides O2N—N=C(R)Cl (R = SMe, Phth; Phth is phthalimide) by the reaction of O2N—N=C(R)SMe with SO2Cl2. The reaction of O2N—N=C(SMe)Cl with potassium phthalimide leads to the replacement of the Cl atom by the phthalimide moiety. The compounds O2N—N=C(Phth)Cl and O2N—N=C(Phth)SMe were studied by X-ray diffraction and quantum chemical methods. The C=N—N and NO2 groups in the O2N—N=C(Phth)Cl molecule were found to be completely orthogonal to each other. The explanation of this fact was proposed.

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. E. G. Bozzi, C. Shiue, L. B. Clapp, J. Org. Chem., 1973, 38, 56.

    Article  CAS  Google Scholar 

  2. L. Brandsma, R. L. P. de Jong, H. D. VerKruijsse, Synthesis, 1985, 10, 948.

    Article  Google Scholar 

  3. W. D. Habicher, R. Mayer, Z. Chem., 1968, 8, 459.

    Article  CAS  Google Scholar 

  4. US Pat. 5453529; Chem. Abstr., 1996, 124, 55973d.

    Google Scholar 

  5. V. N. Petrik, N. V. Kondratenko, L. M. Yagupolskii, J. Fluor. Chem., 2003, 124, 151.

    Article  CAS  Google Scholar 

  6. I. V. Anan´yev, Yu. V. Nelyubina, A. A. Korlyukov, P. Yu. Barzilovich, M. Yu. Antipin, S. M. Aldoshin, K. A. Lyssenko, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2161

    Article  Google Scholar 

  7. I. V. Anan´yev, Izv. Akad. Nauk, Ser. Khim., 2011, 2120].

    Google Scholar 

  8. I. V. Anan´yev, K. A. Lyssenko, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 1270

    Article  Google Scholar 

  9. I. V. Anan´yev, Izv. Akad. Nauk, Ser. Khim., 2014, 1270].

    Google Scholar 

  10. K. A. Lyssenko, Mendeleev Commun., 2012, 22, 1.

    Article  CAS  Google Scholar 

  11. E. Munoz, A. M. Benito, L. C. Estepa, J. Fernandez, Y. Maniette, M. T. Martinez, G. F. de la Fuente, H. Liu, C. M. Silva, E. A. Macedo, E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett., 1998, 285, 170.

    Article  Google Scholar 

  12. E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, E. Molins, Chem. Phys. Lett., 2001, 336, 457.

    Article  CAS  Google Scholar 

  13. R. Taylor, F. H. Allen, Statistical and Numerical Methods of Data Analysis/Structure Correlation, Verlag Chemie, Weinheim, 1994.

    Google Scholar 

  14. A. M. Churakov, S. L. Ioffe, V. A. Tartakovsky, Mendeleev Commun., 1996, 20.

    Google Scholar 

  15. I. S. Bushmarinov, K. A. Lyssenko, M. Yu. Antipin, Russ. Chem. Rev., 2009, 78, 283

    Article  CAS  Google Scholar 

  16. I. S. Bushmarinov, Usp. Khim., 2009, 78, 307].

    Article  Google Scholar 

  17. R. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, New York, 1944, 458 pp.

    Google Scholar 

  18. S. I. Molotov, A. S. Kulikov, Yu. A. Strelenko, N. N. Makhova, K. A. Lyssenko, Russ. Chem. Bull. (Int. Ed.), 2003, 52, 1829

    Article  CAS  Google Scholar 

  19. S. I. Molotov, Izv. Akad. Nauk, Ser. Khim., 2003, 1734].

    Google Scholar 

  20. K. Yu. Suponitsky, K. A. Lyssenko, M. Yu. Antipin, N. S. Aleksandrova, A. B. Sheremetev, T. S. Novikova, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 2129

    Article  CAS  Google Scholar 

  21. K. Yu. Suponitsky, Izv. Akad. Nauk, Ser. Khim., 2009, 2065].

    Google Scholar 

  22. G. M. Sheldrick, Acta Crystallogr., Sect A, 2008, 64, 112.

    Article  CAS  Google Scholar 

  23. A. Volkov, P. Macchi, L. J. Farrugia, C. Gatti, P. Mallinson, T. Richter, T. Koritsanszky, XD2006, A Computer Program Package for Multipole Refinement, Topological Analysis of Charge Densities and Evaluation of Intermolecular Energies from Experimental and Theoretical Structure Factors, 2006.

    Google Scholar 

  24. D. A. Kirzhnits, Yu. E. Lozovik, G. V. Shpatakovskaya, Usp. Fiz. Nauk, 1975, 117, 3

    Article  CAS  Google Scholar 

  25. D. A. Kirzhnits, Soviet Physics-Uspekhi (Engl. Transl.), 1975, 117].

    Google Scholar 

  26. A. Stash, V. Tsirelson, WinXPRO, A Program for Calculation of the Crystal and Molecular Properties Using the Model Electron Density, Mendeleev University of Chemical Technology, Moscow, 2001.

    Google Scholar 

  27. A. Stash, V. G. Tsirelson, J. Appl. Crystallogr., 2002, 35, 371.

    Article  CAS  Google Scholar 

  28. M. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, J. Montgomery, Jr., T. Vreven, K. Kudin, J. Burant, J. Millam, S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. Knox, H. Hratchian, J. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. Stratmann, O. Yazyev, A. Austin, R. Cammi, C. Pomelli, J. Ochterski, P. Ayala, K. Morokuma, G. Voth, P. Salvador, J. Dannenberg, V. Zakrzewski, S. Dapprich, A. Daniels, M. Strain, O. Farkas, D. Malick, A. Rabuck, K. Raghavachari, J. Foresman, J. Ortiz, Q. Cui, A. Baboul, S. Clifford, J. Cioslowski, B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Martin, D. Fox, T. Keith, M. Al-Laham, C. Peng, A. Nanayakkara, M. Challacombe, P. Gill, B. Johnson, W. Chen, M. Wong, C. Gonzalez, J. Pople, Gaussian 03, Revision C.02, Gaussian Inc., Wallingford CT, 2004.

    Google Scholar 

  29. C. Adamo, V. Barone, J. Chem. Phys., 1999, 110, 6158.

    Article  CAS  Google Scholar 

  30. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev., 2005, 105, 2999.

    Article  CAS  Google Scholar 

  31. A. A. Korlyukov, K. A. Lyssenko, M. Yu. Antipin, V. N. Kirin, E. A. Chernyshev, S. P. Knyazev, Inorg. Chem., 2002, 41, 5043.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    O. V. Anikin, M. S. Klenov, A. M. Churakov, Yu. A. Strelenko & V. A. Tartakovsky

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    I. V. Anan´yev & K. A. Lyssenko

Authors
  1. O. V. Anikin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. S. Klenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. M. Churakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. V. Anan´yev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. K. A. Lyssenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yu. A. Strelenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. A. Tartakovsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to O. V. Anikin or K. A. Lyssenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0359—0365, February, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Anikin, O.V., Klenov, M.S., Churakov, A.M. et al. N-nitroimidoyl chlorides: synthesis and structure. Russ Chem Bull 64, 359–365 (2015). https://doi.org/10.1007/s11172-015-0869-7

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0869-7

Keywords

Search

Navigation