Skip to main content
SpringerLink
Log in

Anisyl-, aminophenyl-, and naphthylmethylsilatranes revisited

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Three Si-substituted silatranes were synthesized in order to rectify their structure with particular attention to the length of the N–Si intramolecular dative bond. DFT calculations of potential energy profile as a function of the N–Si distance and the structure of HOMO were considered. The latter was found to vary its localization depending on the electron-donating properties of the substituent and the N–Si distance.

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

Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6

Similar content being viewed by others

Notes

  1. Unpublished results.

References

  1. Baltkais, N. J.; Voronkov, M. G.; Zelchan, G. I. Izv. Akad. Nauk Latv. SSR, Ser. Khim. 1964, 102; Chem. Abstr. 1964, 61, 57120.

  2. Voronkov, M. G.; Dyakov, V. M.; Kirpichenko, S. V. J. Organomet. Chem. 1982, 233, 1.

    Article  CAS  Google Scholar 

  3. Pestunovich, V.; Kirpichenko, S.; Voronkov, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z.; Apeloig, Y., Eds; John Wiley & Sons: Chichester, 1998, Vol. 2, p. 1447.

  4. Verkade, J. G. Coord. Chem. Rev. 1994, 137, 233.

    Article  CAS  Google Scholar 

  5. Tandura, S. N.; Voronkov, M. G.; Alekseev, N. V. Top. Curr. Chem. 1986, 131, 99.

    Article  CAS  Google Scholar 

  6. Trofimov, A. B.; Zakrzewski, V. G.; Dolgounitcheva, O.; Ortiz, J. V.; Sidorkin, V. F.; Belogolova, E. F. ; Belogolov, M.; Pestunovich, V. A. J. Am. Chem. Soc. 2005, 127, 986.

    Article  CAS  Google Scholar 

  7. Sidorkin, V. F.; Pestunovich, V. A.; Voronkov, M. G. Dokl. Akad. Nauk SSSR 1977, 235, 1363.; Chem. Abstr. 1977, 87, 173187.

  8. Sidorkin, V. F.; Pestunovich, V. A.; Voronkov, M. G. Russ. Chem. Rev. 1980, 49, 414. [Usp. Khim. 1980, 49, 789.]

  9. Broka, K.; Stradiņš, J.; Glezer, V.; Zelčāns, G.; Lukevics, E. J. Electroanal. Chem. 1993, 351, 199.

    Article  CAS  Google Scholar 

  10. Broka, K.; Glezer, V.; Stradins, J.; Zelcans, G. Zh. Obshch. Khim. 1991, 61, 1374.

    CAS  Google Scholar 

  11. Jouikov, V. ECS Trans. 2010, 28(12), 5.

    Article  CAS  Google Scholar 

  12. Peureux, C.; Jouikov, V. Chem.–Eur. J. 2014, 20, 9290.

  13. Soualmi, S.; Ignatovich, L.; Jouikov, V. Appl. Organomet. Chem. 2010, 24, 865.

    Article  CAS  Google Scholar 

  14. Ignatovich, L.; Jouikov, V. J. Organomet. Chem. 2014, 751, 546.

    Article  CAS  Google Scholar 

  15. Zöller, T.; Dietz, C.; Iovkova-Berends, L.; Karsten, O.; Bradtmöller, G.; Wiegand, A.-K.; Wang, Y.; Jouikov, V.; Jurkschat, K. Inorg. Chem. 2012, 51, 1041.

    Article  Google Scholar 

  16. Puri, J. K.; Singh, R.; Chahal, V. K. Chem. Soc. Rev. 2011, 40, 1791.

    Article  CAS  Google Scholar 

  17. Voronkov, M. G.; Dyakov, V. M.; Kirpichenko, S. V. J. Organomet. Chem. 1982, 233, 1.

    Article  CAS  Google Scholar 

  18. Voronkov, M. G.; Dyakov, V. M. Silatranes [in Russian]; Nauka: Novosibirsk, 1978.

    Google Scholar 

  19. Voronkov, M. G.; Kuznetsova, G. A.; Baryshok, V. P. Rus. J. Gen. Chem. 1983, 53, 1512. [Zh. Obshch. Khim. 1983, 53, 1682.]

  20. Frye, C. L.; Vogel, G. E.; Hall, J. A. J. Am. Chem. Soc. 1961, 83, 996.

    Article  CAS  Google Scholar 

  21. Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328, C17.

    Article  CAS  Google Scholar 

  22. Zhuo, R.; Lu, Z.-R.; Liao, J.; Shen, L.-F. J. Organomet. Chem. 1993, 446, 107.

    Article  CAS  Google Scholar 

  23. Lukevics, E.; Ignatovich, L. M. Chem. Heterocycl. Compd. 1992, 28, 603. [Khim. Geterotsikl. Soedin. 1992, 725.]

  24. Corriu, R. J. In Frontiers of Organosilicon Chemistry; Bassindale, A. R.; Gaspar P. P., Eds.; RSC: Cambridge, 1991, p.126 .

  25. Armarego, W. L. E.; Chai, C. L. L. Purification of Organic Chemicals; Butterworth-Heinemann: Amsterdam, 2003, 5th d.; p. 215.

  26. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: Toronto, 2000, p. 31.

    Google Scholar 

  27. Chernyshev, E. P.; Knazev, S. P.; Kirin, V. N.; Vasiliev, I. M.; Alekseev, N. V. Rus. J. Gen. Chem. 2004, 74, 58. [Zh. Obshch. Khim. 2004, 74, 65.]

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

    Article  CAS  Google Scholar 

  29. Amatore, C. In Organic Electrochemistry; Lund, H.; Hammerich, O., Eds.; Marcel Dekker: New York, 2001, 4th ed., p. 1.

  30. Belogolova, E. F.; Vakul'skaya, T. I.; Sidorkin, V. F. Phys. Chem. Chem. Phys. 2015, 17, 12735.

    Article  CAS  Google Scholar 

  31. Sidorkin, V. F.; Belogolova, E. F.; Doronina, E. P. Phys. Chem. Chem. Phys. 2015, 17, 26225.

    Article  CAS  Google Scholar 

  32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T., Jr.; 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.; 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.; Pople, J. A. Gaussian 03, Revision B.01; Gaussian, Inc.: Pittsburgh, 2003.

  33. Brennan, B. J., Gust, D., Brudvig, G. W. Tetrahedron Lett. 2014, 55, 1062.

    Article  CAS  Google Scholar 

  34. Voronkov, M. G.; Zelcan, G. I. Chem. Heterocycl. Compd. 1969, 5, 34. [Khim. Geterotsikl. Soedin. 1969, 43.]

  35. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

  36. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

  37. van der Sluis, P.; Spek, A. L. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, A46, 194.

  38. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.

    Article  CAS  Google Scholar 

Download references

The authors gratefully acknowledge the support of this research by InnovaBalt program and the Latvian Council for Science (Project 225/2012).

Author information

Authors and Affiliations

  1. UMR 6226 ISCR, University of Rennes I, 35042, Rennes, France

    Yu Wang, Thierry Roisnel & Viatcheslav Jouikov

  2. Latvian Institute of Organic Synthesis, 21 Aizkraukles St, Riga, LV-1006, Latvia

    Vitalijs Romanovs, Jana Spura & Lubova Ignatovica

Authors
  1. Yu Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vitalijs Romanovs
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jana Spura
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lubova Ignatovica
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Thierry Roisnel
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Viatcheslav Jouikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Vitalijs Romanovs or Viatcheslav Jouikov.

Additional information

Lubova Ignatovica is Deceased

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(8), 546–550

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 241 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, Y., Romanovs, V., Spura, J. et al. Anisyl-, aminophenyl-, and naphthylmethylsilatranes revisited. Chem Heterocycl Comp 52, 546–550 (2016). https://doi.org/10.1007/s10593-016-1928-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1928-1

Keywords

Search

Navigation