Skip to main content
SpringerLink
Log in

Reaction of 2-[Aryl(alkyl)amino]malonates with Chloroethynylphosphonates

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

Abstract

Preparative limitations of the reaction of chloroethynylphosphonates with 2-(alkylamino)malonates have been established. Unlike the reaction of chloroethynylphosphonates with 2-(arylamino)malonates which involve only the carbon nucleophilic center, 2-(alkylamino)malonates react through both carbon and nitrogen atoms. The geometric structural, energetic, and charge parameters of the optimized structures of aliphatic and aromatic diethyl 2-aminomalonates have been determined by quantum chemical calculations using Gaussian 03 software, and pKa values for both nucleophilic centers in their molecules have been calculated.

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. Ionin, B.I. and Petrov, A.A., Zh. Obshch. Khim., 1965, vol. 35, no. 11, p. 1917.

    CAS  Google Scholar 

  2. Ionin, B.I. and Petrov, A.A., Zh. Obshch. Khim., 1965, vol. 35, no. 12, p. 225.

    Google Scholar 

  3. Petrov, A.A., Dogadina, A.V., Ionin, B.I., Garibina, V.A., and Leonov, A.A., Russ. Chem. Rev., 1983, vol. 52, no. 11, p. 1030.

    Article  Google Scholar 

  4. Garibina, V.A., Leonov, A.A., Dogadina, A.V., Ionin, B.I., and Petrov, A.A., Zh. Obshch. Khim., 1985, vol. 55, no. 9, p. 1994.

    CAS  Google Scholar 

  5. Garibina, V.A., Leonov, A.A., Dogadina, A.V., Ionin, B.I., and Petrov, A.A., Zh. Obshch. Khim., 1987, vol. 57, no. 7, p. 1481.

    CAS  Google Scholar 

  6. Petryanina, A.I., Didkovskii, N.G., Dogadina, A.V., and Ionin, B.I., Russ. J. Gen. Chem., 2006, vol. 76, no. 9, p. 1516. https://doi.org/10.1134/S1070363206090271

    Article  CAS  Google Scholar 

  7. Khramchikhin, V.A., Yakobson, G.V., Dogadina, A.V., Khramchikhin, A.V., Ionin, B.I., Russ. J. Gen. Chem., 2010, vol. 80, no. 2. p. 364. https://doi.org/10.1134/S1070363210020301

    Article  CAS  Google Scholar 

  8. Khramchikhin, V.A., Didkovskii, N.G., Khramchikhin, A.V., Dogadina, A.V., and Ionin, B.I., Russ. J. Gen. Chem., 2011, vol. 81, no. 8, p. 1635. https://doi.org/10.1134/S1070363211080093

    Article  CAS  Google Scholar 

  9. Didkovskii, N.G., Cand. Sci. (Chem.) Dissertation, St. Petersburg, 2007.

  10. Khramchikhin, V.A., Dogadina, A.V., Khramchikhin, A.V., and Ionin, B.I., Russ. J. Gen. Chem., 2012, vol. 82, no. 4, p. 776. https://doi.org/10.1134/S1070363212040299

    Article  CAS  Google Scholar 

  11. Erkhitueva, E.B., Dogadina, A.V., Khramchikhin, A.V., and Ionin, B.I., Russ. J. Gen. Chem., 2011, vol. 81, no. 11, p. 2377. https://doi.org/10.1134/S1070363211110296

    Article  CAS  Google Scholar 

  12. Erkhitueva, E.B., Dogadina, A.V., Khramchihin, A.V., and Ionin, B.I., Tetrahedron Lett., 2012, vol. 53, no. 33, p. 4304. https://doi.org/10.1016/j.tetlet.2012.05.157

    Article  CAS  Google Scholar 

  13. Erkhitueva, E.B., Dogadina, A.V., Khramchikhin, A.V., and Ionin, B.I., Russ. J. Org. Chem., 2013, vol. 49, no. 4, p. 580. https://doi.org/10.1134/S1070428013040155

    Article  CAS  Google Scholar 

  14. Erkhitueva, E.B., Dogadina, A.V., Khramchihin, A.V., and Ionin, B.I., Tetrahedron Lett., 2013, vol. 54, no. 38, p. 5174. https://doi.org/10.1016/j.tetlet.2013.07.032

    Article  CAS  Google Scholar 

  15. Egorova, A.V., Viktorov, N.B., Starova, G.L., Svintsitskaya, N.I., Garabadziu, A.V., and Dogadina, A.V., Tetrahedron Lett., 2017, vol. 58, p. 2997. https://doi.org/10.1016/j.tetlet.2017.06.062

    Article  CAS  Google Scholar 

  16. Dogadina, A.V., Erkhitueva, E.B., and Ionin, B.I., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, no. 3, p. 716. https://doi.org/10.1007/s11172-014-0497-7

    Article  CAS  Google Scholar 

  17. Egorova, A.V., Viktorov, N.B., Starova, G.L., Svintsitskaya, N.I., Garabadziu, A.V., and Dogadina, A.V., Tetrahedron Lett., 2017, vol. 58, p. 2997. https://doi.org/10.1016/j.tetlet.2017.06.062

    Article  CAS  Google Scholar 

  18. Lyamenkova, D.V., Viktorov, N.B., and Dogadina, A.V., Russ. J. Gen. Chem., 2015, vol. 85, no. 2, p. 500. https://doi.org/10.1134/S1070363215020243

    Article  CAS  Google Scholar 

  19. Ripin, D.H. and Evans, D.A., Evans pKa Table. http://www.chem.wisc.edu/areas/reich/pkatable/index.htm.

  20. Kaljurand, I., Kutt, A., Soov, L., Rodima, T., Maemets, V., Leito, I., and Koppel, I.A., J. Org. Chem., 2005, vol. 70, p. 1019. https://doi.org/10.1021/jo048252w

    Article  CAS  Google Scholar 

  21. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., 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, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision C.02, Wallingford CT: Gaussian, 2003.

    Google Scholar 

Download references

Acknowledgments

The authors thank V.A. Ostrovskii (St. Petersburg State Institute of Technology) for valuable discussion. The study was carried out using the facilities of the Engineering Center of the St. Petersburg State Institute of Technology.

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project no. 19-03-00 365) in the framework of the base part of state assignment of the Ministry of Science and Higher Education of the Russian Federation (project no. 4.5554.2017/8.9).

Author information

Authors and Affiliations

  1. St. Petersburg State Institute of Technology, St. Petersburg, Russia

    A. V. Egorova & A. V. Dogadina

  2. Scientific Research Center for Environmental Safety Russian, Academy of Sciences, St. Petersburg, Russia

    A. V. Egorova

  3. St. Petersburg State University, St. Petersburg, Russia

    I. A. Boyarskaya

Authors
  1. A. V. Egorova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. A. Boyarskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Dogadina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Dogadina.

Ethics declarations

No conflict of interest was declared by the authors.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 10, pp. 1504–1510.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Egorova, A.V., Boyarskaya, I.A. & Dogadina, A.V. Reaction of 2-[Aryl(alkyl)amino]malonates with Chloroethynylphosphonates. Russ J Gen Chem 89, 2005–2009 (2019). https://doi.org/10.1134/S1070363219100049

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219100049

Keywords

Search

Navigation