Skip to main content
SpringerLink
Log in

Molecular structure of 6-cyclopentyl-1,5-diazabicyclo[3.1.0]hexane studied by gas electron diffraction

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

Abstract

6-Cyclopentyl-1,5-diazabicyclo[3.1.0]hexane was synthesized for the first time, and its molecular structure was studied by gas electron diffraction and quantum chemistry. It was found that 6-cyclopentyl-1,5-diazabicyclo[3.1.0]hexane in vapors exists as a form with the perpendicular arrangement of the cycles.

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. Vitaku, D. T. Smith, J. T. Njardarson, J. Med. Chem., 2014, 57, 10257; DOI: https://doi.org/10.1021/jm501100b.

    Article  CAS  PubMed  Google Scholar 

  2. C. J. Paget, C. S. Davis, J. Med. Chem., 1964, 7, 626; DOI: https://doi.org/10.1021/jm00335a012.

    Article  CAS  PubMed  Google Scholar 

  3. X. Zhang, L. Shen, Y. Luo, R. Jiang, H. Sun, J. Liu, T. Fang, H. Fan, Z. Liu, Ind. Eng. Chem. Res., 2017, 56, 11, 2883; DOI: https://doi.org/10.1021/acs.iecr.6b04842.

    Google Scholar 

  4. K. Y. Suponitsky, A. F. Smol’yakov, I. V. Ananyev, A. V. Khakhalev, A. A. Gidaspov, A. B. Sheremetev, Chemistry-Select, 2020, 5, 14543; DOI: https://doi.org/10.1002/slct.202004020.

    CAS  Google Scholar 

  5. M. S. Klenov, D. B. Lempert, A. A. Konnov, D. A. Gulyaev, I. A. Vatsadze, T. S. Kon’kova, Yu. N. Matyushin, E. A. Miroshnichenko, A. B. Vorobyev, Ya. O. Inozemtsev, A. V. Inozemtsev, A. N. Pivkina, A. O. Dmitrienko, V. A. Tartakovsky, Russ. Chem. Bull., 2022, 71, 1123; DOI: https://doi.org/10.1007/s11172-022-3512-4.

    Article  CAS  Google Scholar 

  6. Y. V. Vishnevskiy, N. Vogt, J. Vogt, A. N. Rykov, V. V. Kuznetsov, N. N. Makhova, L. V. Vilkov, J. Phys. Chem. A, 2008, 112, 5243; DOI: https://doi.org/10.1021/jp801346v.

    Article  CAS  PubMed  Google Scholar 

  7. L. S. Khaikin, G. G. Ageev, A. N. Rykov, O. E. Grikina, I. F. Shishkov, I. V. Kochikov, V. V. Kuznetsov, N. N. Makhova, S. S. Bukalov, L. A. Leites, Phys. Chem. Chem. Phys., 2020, 22, 22477; DOI: https://doi.org/10.1039/D0CP04005C.

    Article  CAS  PubMed  Google Scholar 

  8. I. I. Marochkin, E. P. Altova, V. V. Kuznetsov, A. N. Rykov, I. F. Shishkov, Mendeleev Commun., 2022, 32, 474; DOI: https://doi.org/10.1016/j.mencom.2022.07.015.

    Article  CAS  Google Scholar 

  9. I. N. Kolesnikova, V. V. Kuznetsov, A. S. Goloveshkin, N. A. Chegodaev, N. N. Makhova, I. F. Shishkov, Struct. Chem., 2021, 32, 2303; DOI: https://doi.org/10.1007/s11224-021-01806-x.

    Article  CAS  Google Scholar 

  10. A. O. Chagarovskiy, V. V. Kuznetsov, O. A. Ivanova, A. S. Goloveshkin, I. I. Levina, N. N. Makhova, I. V. Trushkov, Eur. J. Org. Chem., 2019, 31–32, 5475; DOI: https://doi.org/10.1002/ejoc.201900579.

    Article  Google Scholar 

  11. Yu. V. Vishnevskiy, UNEX version 1.6, unexprog.org, 2022.

  12. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. 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. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh, 2003.

    Google Scholar 

  13. A. D. Becke, J. Chem. Phys., 1993, 98, 5648; DOI: https://doi.org/10.1063/1.464913.

    Article  CAS  Google Scholar 

  14. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B, 1988, 37, 785; DOI: https://doi.org/10.1103/PhysRevB.37.785.

    Article  CAS  Google Scholar 

  15. C. Møller, M. S. Plesset, Phys. Rev., 1934, 46, 618; DOI: https://doi.org/10.1103/PhysRev.46.618.

    Article  Google Scholar 

  16. T. H. Dunning, J. Chem. Phys., 1989, 90, 1007; DOI: https://doi.org/10.1063/1.456153.

    Article  CAS  Google Scholar 

  17. V. A. Sipachev, J. Mol. Struct.: Theochem, 1985, 121, 143; DOI: https://doi.org/10.1016/0166-1280(85)80054-3.

    Article  Google Scholar 

  18. W. J. Adams, H. J. Geise, L. S. Bartell, J. Am. Chem. Soc., 1970, 92, 17, 5013; DOI: https://doi.org/10.1021/ja00720a001.

    Google Scholar 

  19. G. G. Ageev, A. N. Rykov, O. E. Grikina, I. F. Shishkov, I. V. Kochikov, V. V. Kuznetsov, N. N. Makhova, S. S. Bukalov, Struct. Chem., 2022, 33, 113; DOI: https://doi.org/10.1007/s11224-021-01828-5.

    Article  CAS  Google Scholar 

  20. E. J. Ocola, L. E. Bauman, J. Laane, J. Phys. Chem. A, 2011, 115, 24, 6531; DOI: https://doi.org/10.1021/jp2032934.

    Article  Google Scholar 

  21. A. V. Karnik, M. Hasan, Stereochemistry. A Three-Dimensional Insight, Elsevier, 2021, 620 pp.

  22. Yu. V. Vishnevskiy, J. Schwabedissen, A. N. Rykov, V. V. Kuznetsov, N. N. Makhova, J. Phys. Chem. A, 2015, 119, 10871; DOI: https://doi.org/10.1021/acs.jpca.5b08228.

    Article  CAS  PubMed  Google Scholar 

  23. F. Weinhold, C. R. Landis, Discovering Chemistry with Natural Bond Orbitals, John Wiley & Sons, New Jersey, 2012, p. 132.

    Book  Google Scholar 

Download references

Funding

This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-03-00747 A).

Author information

Authors and Affiliations

  1. Department of Chemistry, Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russia

    E. P. Al’tova, I. I. Marochkin, P. Yu. Sharanov, A. N. Rykov & I. F. Shishkov

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

    V. V. Kuznetsov

Authors
  1. E. P. Al’tova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. I. Marochkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. Yu. Sharanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. N. Rykov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. V. Kuznetsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. F. Shishkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. P. Al’tova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2231–2235, October, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Al’tova, E.P., Marochkin, I.I., Sharanov, P.Y. et al. Molecular structure of 6-cyclopentyl-1,5-diazabicyclo[3.1.0]hexane studied by gas electron diffraction. Russ Chem Bull 71, 2231–2235 (2022). https://doi.org/10.1007/s11172-022-3650-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3650-8

Key words

Search

Navigation