Skip to main content
SpringerLink
Log in

Complexes of the Lewis Acid Ga[N(C6F5)2]3 with Acetonitrile and Pyridine

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

Abstract

Reaction of the Lewis acid Ga[N(C6F5)2]3 with acetonitrile and pyridine in toluene solution was characterized by 19F NMR. Quantum chemical calculations show that the shorter donor-acceptor bond in the acetonitrile complex is weaker by 73 kJ/mol than the longer donor-acceptor bond in the pyridine complex, which is consistent with partial dissociation of the Ga[N(C6F5)2]3·MeCN complex in toluene.

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
Fig. 1.

Similar content being viewed by others

REFERENCES

  1. Fringuelli, F., Piermatti, O., Pizzo, F. and Vaccaro, L., Eur. J. Org. Chem., 2001, vol. 3, p. 439. https://doi.org/10.1002/1099-0690(200102)2001:3<439::AID-EJOC439>3.0.CO;2-B

    Article  Google Scholar 

  2. Suyama, K., Matsumoto, K., and Katsuki, T., Heterocycles, 2009, vol. 77, p. 817. https://doi.org/10.3987/COM-08-S(F)93

    Article  CAS  Google Scholar 

  3. Flynn, A.J., Fordband, A., and Maguire, A.R., Org. Biomol. Chem., 2020, vol. 18, p. 2549. https://doi.org/10.1039/c9ob02587a

    Article  CAS  PubMed  Google Scholar 

  4. Pellissier, H., Org. Biomol. Chem., 2017, vol. 15, p. 4750. https://doi.org/10.1039/c7ob00903h

    Article  CAS  PubMed  Google Scholar 

  5. Stephan, D.W., J. Am. Chem. Soc., 2015, vol. 137, p. 10018. https://doi.org/10.1021/jacs.5b06794

    Article  CAS  PubMed  Google Scholar 

  6. Riddlestone, I.M., Kraft, A., Schaefer, J., and Krossing, I., Angew. Chem. Int. Ed., 2018, vol. 57, p. 13982. https://doi.org/10.1002/anie.201710782

    Article  CAS  Google Scholar 

  7. Haartz, J.C. and McDaniel, D.H., J. Am. Chem. Soc., 1973, vol. 95, p. 8562. https://doi.org/10.1021/ja00807a011

    Article  CAS  Google Scholar 

  8. Olah, G.A., Prakash, G.K.S., and Sommer, J., Science, 1979, vol. 206, p. 13. https://doi.org/10.1126/science.206.4414.13

    Article  CAS  PubMed  Google Scholar 

  9. Blander, M., Epel, L.G., Fraas, A.P., and Newton, R.F., Aluminum Chloride as a Thermodynamic Working Fluid and Heat Transfer Medium, Oak Ridge: Oak Ridge National Lab., 1959. 29 p. https://doi.org/10.2172/4209651

  10. Müller, L.O., Himmel, D., Stauffer, J., Steinfeld, G., Slattery, J., Santiso-Quinones, G., Brecht, V., and Krossing, I., Angew. Chem. Int. Ed., 2008, vol. 47, p. 7659. https://doi.org/10.1002/anie.200800783

    Article  CAS  Google Scholar 

  11. Kögel, J.F., Timoshkin, A.Y., Schroder, A., Lork, E., and Beckmann, J., Chem. Sci., 2018, vol. 9, p. 8178. https://doi.org/10.1039/c8sc02981d

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Kögel, J.F., Sorokin, D.A., Khvorost, A., Scott, M., Harms, K., Himmel, D., Krossing, I., and Sundermeyer, J., Chem. Sci., 2018, vol. 9, p. 245. https://doi.org/10.1039/c7sc03988c

    Article  CAS  PubMed  Google Scholar 

  13. Böhrer, H., Trapp, N., Himmel, D., Schleep, M., and Krossing, I., Dalton Trans., 2015, vol. 44, p. 7489. https://doi.org/10.1039/C4DT02822H

    Article  CAS  PubMed  Google Scholar 

  14. Guryanova, E.N., Goldstein, I.P., and Romm, I.P., Donor-Acceptor Bond, New York, Wiley, 1975.

  15. Gutmann, V., Coord. Chem. Rev., 1976, vol. 18, p. 225. https://doi.org/10.1016/S0010-8545(00)82045-7

    Article  CAS  Google Scholar 

  16. Davydova, E.I., Virovets, A.V., Peresypkina, E.V., Kazakov, I.V., and Timoshkin, A.Y., Russ. Chem. Bull., 2020, vol. 69, p. 84. https://doi.org/10.1007/s11172-020-2726-6

    Article  CAS  Google Scholar 

  17. Timoshkin, A.Y., Bodensteiner, M., Sevastianova, T.N., Lisovenko, A.S., Davydova, E.I., Scheer, M., Graßl, C., and Butlak, A.V., Inorg. Chem., 2012, vol. 51, p. 11602. https://doi.org/10.1021/ic301507c

    Article  CAS  PubMed  Google Scholar 

  18. Timoshkin, A.Y. and Frenking, G., Organometallics, 2008, vol. 27, p. 371. https://doi.org/10.1021/om700798t

    Article  CAS  Google Scholar 

  19. Shcherbina, N.A., Pomogaeva, A.V., Lisovenko, A.S., Kazakov, I.V., Gugin, N.Y., Khoroshilova, O.V., Kondrat’ev, Y.V., and Timoshkin, A.Y., Z. Anorg. Allg. Chem., 2020, vol. 646, p. 873. https://doi.org/10.1002/zaac.202000030

    Article  CAS  Google Scholar 

  20. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., and Fox, D.J., Gaussian 16, Revision A.03; Gaussian, Inc.: Wallingford, CT. 2016.

  21. Zhao, Y. and Truhlar, D.G., Theor. Chem. Acc., 2008, vol. 120, p. 215. https://doi.org/10.1007/s00214-007-0310-x

    Article  CAS  Google Scholar 

  22. Weigend, F. and Ahlrichs, R., Phys. Chem. Chem. Phys., 2005, vol. 7, p. 3297. https://doi.org/10.1039/B508541A

    Article  CAS  PubMed  Google Scholar 

  23. Reed, A.E., Curtiss, L.A., and Weinhold, F., Chem. Rev., 1988, vol. 88, p. 899. https://doi.org/10.1021/cr00088a005

    Article  CAS  Google Scholar 

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

  25. Marenich, A.V., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. (B), 2009, vol. 113, p. 6378. https://doi.org/10.1021/jp810292n

    Article  CAS  Google Scholar 

  26. Cancès, E., Mennucci, B., and Tomasi, J., J. Chem. Phys., 1997, vol. 107, p. 3032. https://doi.org/10.1063/1.474659

    Article  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors express their gratitude to the research group of Professor J. Beckman (University of Bremen, Germany), in particular J. Kögel, D. Duvinage, F. Feige, and M. Olaru for their assistance in the experimental part of the work.

Funding

The work was supported by the Russian science Foundation (grant no. 18-13-00196) using equipment from the Computing center of St. Petersburg state University and the Chemistry center of the University of Bremen (UBS-Zentrum für Chemie).

Author information

Authors and Affiliations

  1. St. Petersburg State University, 199034, St. Petersburg, Russia

    A. S. Zavgorodnii, А. V. Pomogaeva & A. Y. Timoshkin

Authors
  1. A. S. Zavgorodnii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. А. V. Pomogaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Y. Timoshkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Y. Timoshkin.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zavgorodnii, A.S., Pomogaeva, А.V. & Timoshkin, A.Y. Complexes of the Lewis Acid Ga[N(C6F5)2]3 with Acetonitrile and Pyridine. Russ J Gen Chem 90, 2305–2311 (2020). https://doi.org/10.1134/S1070363220120130

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220120130

Keywords:

Search

Navigation