Skip to main content
SpringerLink
Log in

Conformational analysis of 2-substituted nitroethenes

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

Experimental and theoretical conformational analysis of polyfunctional 2-substituted nitroethenes was carried out by the method of dipole moments and density functional theory calculations. It was established that the nitro and ester (or trichloromethyl) groups are trans-arranged in the molecules of 2-trichloromethyl-(ethoxycarbonyl)-1-nitro- and 1-bromo-1-nitroethenes, i.e., nitroalkenes have E-configuration, their bromo-containing analogues have Z-configuration, and s-cis-orientation of the C=C and C=O double bonds is preferred for nitroacrylates. 2,3-Dibromo-3-nitroacrylates have untrivial Z-configuration in solution.

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

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Perekalin VV, Lipina ES, Berestovitskaya VM, Efremov DA (1994) Nitroalkenes: conjugated nitro compounds. Wiley, London

    Google Scholar 

  2. Ono N (2001) The nitro group in organic synthesis. VCH, New York

    Book  Google Scholar 

  3. Feuer H (ed) (1969) The chemistry of the nitro and nitroso groups. Interscience, New York

    Google Scholar 

  4. Barret GM (1991) Chem Soc Rev 20:95

    Article  Google Scholar 

  5. Berestovitskaya VM, Zobacheva MM, Vasil’eva VS (2002) Izv Ross Gos Ped Univ 2:133

    Google Scholar 

  6. Berestovitskaya VM, Bel’skii VK, Macmillan JG, Makarenko SV, Trukhin EV (1999) Zh Org Khim 69:835

    Google Scholar 

  7. Nguyen NV, Baum K (1992) Tetrahedron Lett 33:2949

    Article  CAS  Google Scholar 

  8. Ishmaeva EA, Gazizova AA, Vereshchagina YaA, Chachkov DV, Anisimova NA, Makarenko SV, Smirnova AS, Berestovitskaya VM (2007) Zh Obshch Khim 77:798

    Google Scholar 

  9. Ishmaeva EA, Berestovitskaya VM, Litvinov IA, Vereshchagina YaA, Yarkova EG, Fattakhova GR, Krivolapov DB, Makarenko SV, Trukhin EV, Pavlova IV (2001) Russ J Gen Chem 71:429

    Article  CAS  Google Scholar 

  10. Berestovitskaya VM, Litvinov IA, Ishmaeva EA, Deiko LI, Vereshchagina YaA, Sarkisyan ZM, Gubaidullin AT, Fattakhova GR, Makarenko SV, Berkova GA (2004) Russ J Gen Chem 74:110

    Article  CAS  Google Scholar 

  11. Makarenko SV, Kovalenko KS, Krivolapov DB, Litvinov IA, Berestovitskaya VM (2009) Izv Akad Nauk Ser Khim 1977

  12. Gribov LA, Popov EM (1962) Dokl Akad Nauk SSSR 145:761

    CAS  Google Scholar 

  13. Nigmatullin RSh, Vyaselev MR, Shatunov VS (1964) Zavodskaya Laboratoriya 30:500

    CAS  Google Scholar 

  14. Ishmaeva EA, Vereshchagina YaA, Pavlova IV, Fattakhova GR, Makarenko SV, Trukhin EV, Berestovitskaya VM (2000) Zh Obshch Khim 70:2056

    Google Scholar 

  15. Panfilova LV, Antipin MYu, Churkin YuD, Struchkov YuT (1979) Khim Geterotsikl Soedin 1201

  16. Osipov OA, Minkin VI, Garnovskii AD (1971) Spravochnik po dipol’nym momentam (Dipole moments handbook). Vysshaya Shkola, Moscow

    Google Scholar 

  17. Ishmaeva EA, Zimin MG, Galeeva RM. Pudovik AN (1971) Izv Akad Nauk SSSR Ser Khim 538

  18. Ishmaeva EA, Kharrasova FM, Remizov AB, Pudovik AN (1974) Dokl Akad Nauk SSSR 218:107

    CAS  Google Scholar 

  19. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03. Gaussian Inc, Pittsburgh, PA

    Google Scholar 

Download references

Acknowledgment

This research was supported by the Russian Foundation for Basic Research (Grant No. 10-03-00098-a).

Author information

Authors and Affiliations

  1. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University (KFU), Kremlevskaya, 18, Kazan, 420008, Russia

    Yana A. Vereshchagina & Eleonora A. Ishmaeva

  2. Kazan Branch of Joint Supercomputer Center of Russian Academy of Sciences, Kazan, Russia

    Denis V. Chachkov

  3. Hertzen Russian State Pedagogical University, Saint Petersburg, Russia

    Valentina M. Berestovitskaya

Authors
  1. Yana A. Vereshchagina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Denis V. Chachkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Eleonora A. Ishmaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Valentina M. Berestovitskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yana A. Vereshchagina.

Additional information

Dedicated to memory of Professor L. V. Vilkov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vereshchagina, Y.A., Chachkov, D.V., Ishmaeva, E.A. et al. Conformational analysis of 2-substituted nitroethenes. Struct Chem 22, 357–360 (2011). https://doi.org/10.1007/s11224-010-9728-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-010-9728-1

Keywords

Search

Navigation