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Acenaphthylene-1,2-diamine radical cation. Molecular structure of the [(dpp-BIAN)H2]·+[X]− complex ((dpp-BIAN)H2 is N,N′-bis(2,6-diisopropylphenyl)-acenaphthylene-1,2-diamine; X = Cl or I)

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Abstract

Oxidation of N,N′-bis(2,6-diisopropylphenyl)acenaphthylene-1,2-diamine (dpp-BIAN)H2 with silicon tetrachloride or mercury(II) chloride affords the [(dpp-BIAN)H2]·+[Cl]− compound. The corresponding iodine derivative, [(dpp-BIAN)H2]·+[I]−, was prepared by hydrolysis of the reaction products of the magnesium complex (dpp-BIAN)Mg(THF)3 with tetraiodosilane. X-ray diffraction study demonstrated that the [(dpp-BIAN)H2]·+ radical cation in these compounds chelates the corresponding halide anion.

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References

  1. M. W. van Laren and C. J. Elsevier, Angew. Chem., Int. Ed., 1999, 38, 3715.

    Article  Google Scholar 

  2. R. van Belzen, H. Hoffmann, and C. J. Elsevier, Angew. Chem., Int. Ed., 1997, 36, 1743; (b) G. A. Grasa, R. Singh, E. D. Stevens, and S. P. Nolan, J. Organomet. Chem., 2003, 687, 269.

    Article  Google Scholar 

  3. A. Heumann, L. Giordano, and A. Tenaglia, Tetrahedron Lett., 2003, 44, 1515.

    Article  CAS  Google Scholar 

  4. J. W. Sprengers, M. de Greef, M. A. Duin, and C. J. Elsevier, Eur. J. Inorg. Chem., 2003, 3811.

  5. E. Cherian, E. B. Lobkovsky, and G. W. Coates, Chem. Commun., 2003, 20, 2566; (b) F. Al-Abaidi, Z. Ye, and S. Zhu, Macromol. Chem. Phys., 2003, 204, 1653; (c) V. Fassina, C. Ramminger, M. Seferin, R. S. Mauler, R. F. de Souza, and A. L. Monteiro, Macromol. Rapid Commun., 2003, 24, 667; (d) M. D. Leatherman, S. A. Svejda, L. K. Johnson, and M. Brookhart, J. Am. Chem. Soc., 2003, 125, 3068.

    Article  Google Scholar 

  6. I. Kim, J.-M. Hwang, J. K. Lee, C. S. Ha, and S. I. Woo, Macromol. Rapid Commun., 2003, 24, 508.

    Article  CAS  Google Scholar 

  7. D. Takeuchi, A. Yasuda, and K. Osakada, Dalton Trans., 2003, 2029.

  8. J. Kiesewetter and W. Kaminsky, Chem. Eur. J., 2003, 9, 1750.

    Article  CAS  Google Scholar 

  9. B. Binotti, C. Carfagna, C. Zuccaccia, and A. Macchioni, Chem. Commun., 2005, 92.

  10. B. S. Williams, M. D. Leatherman, P. S. White, and M. Brookhart, J. Am. Chem. Soc., 2005, 127, 5132; (b) J. Merna, J. Cihlar, M. Kucera, A. Deffieux, and H. Cramail, Eur. Polym. J., 2005, 41, 303; (c) W. Liu and M. Brookhart, Organometallics, 2004, 23, 6099; (d) D. H. Camacho, E. V. Salo, J. W. Ziller, and Z. Guan, Angew. Chem., Int. Ed., 2004, 43, 1821.

    Article  CAS  Google Scholar 

  11. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, and G. K. Fukin, Angew. Chem., Int. Ed. Engl., 2003, 42, 3294; (b) I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, V. K. Cherkasov, G. K. Fukin, and M. A. Lopatin, Eur. J. Inorg. Chem., 2004, 388.

    Article  CAS  Google Scholar 

  12. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, G. K. Fukin, S. Dechert, and H. Schumann, Eur. J. Inorg. Chem., 2003, 3336; (b) I. L. Fedushkin, A. G. Morozov, O. V. Rassadin, and G. K. Fukin, Chem. Eur. J., 2005, 11, 5749.

    Google Scholar 

  13. A. N. Lukoyanov, I. L. Fedushkin, M. Hummert, and H. Schumann, Izv. Akad. Nauk, Ser. Khim., 2006, No. 3, 409 [Russ. Chem. Bull., Int. Ed., 2006, 55, No. 3].

  14. H. Schumann, M. Hummert, A. N. Lukoyanov, and I. L. Fedushkin, Organometallics, 2005, 24, 3891; (b) A. N. Lukoyanov, I. L. Fedushkin, M. Hummert, and H. Schumann, Z. Anorg. Allg. Chem., 2006, 632, No. 819.

    Article  CAS  Google Scholar 

  15. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, N. M. Khvoinova, A. Yu. Baurin, S. Dechert, M. Hummert, and H. Schumann, Organometallics, 2004, 23, 3714.

    Article  CAS  Google Scholar 

  16. I. L. Fedushkin, N. M. Khvoinova, A. Yu. Baurin, G. K. Fukin, V. K. Cherkasov, and M. P. Bubnov, Inorg. Chem., 2004, 43, 7807; (b) I. L. Fedushkin, N. M. Khvoinova, A. Yu. Baurin, V. A. Chudakova, A. A. Skatova, V. K. Cherkasov, G. K. Fukin, and E. V. Baranov, Izv. Akad. Nauk, Ser. Khim., 2006, 71 [Russ. Chem. Bull., Int. Ed., 2006, 55, No. 1].

    Article  CAS  Google Scholar 

  17. I. L. Fedushkin, A. A. Skatova, A. N. Lukoyanov, V. A. Chudakova, S. Dechert, M. Hummert, and H. Schumann, Izv. Akad. Nauk, Ser. Khim., 2004, 2641 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2751]; (b) I. L. Fedushkin, V. M. Makarov, E. C. E. Rosenthal, and G. K. Fukin, Eur. J. Inorg. Chem., 2006, 827.

  18. I. L. Fedushkin, A. A. Skatova, V. K. Cherkasov, V. A. Chudakova, S. Dechert, M. Hummert, and H. Schumann, Chem. Eur. J., 2003, 9, 5778.

    Article  CAS  Google Scholar 

  19. I. L. Fedushkin, A. A. Skatova, G. K. Fukin, M. Hummert, and H. Schumann, Eur. J. Inorg. Chem., 2005, 2332.

  20. I. L. Fedushkin, N. M. Khvoinova, A. A. Skatova, and G. K. Fukin, Angew. Chem., Int. Ed., 2003, 42, 5223.

    Article  CAS  Google Scholar 

  21. I. L. Fedushkin, V. A. Chudakova, S. Dechert, M. Hummert, and H. Schumann, Izv. Akad. Nauk, Ser. Khim., 2004, 2634 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2744].

    Google Scholar 

  22. I. L. Fedushkin, N. M. Khvoinova, A. V. Piskunov, G. K. Fukin, M. Hummert, and H. Schumann, Izv. Akad. Nauk, Ser. Khim., 2006, No. 5 [Russ. Chem. Bull., Int. Ed., 2006, 55, No. 5].

  23. I. L. Fedushkin, V. A. Chudakova, A. A. Skatova, N. M. Khvoinova, Yu. A. Kurskii, T. A. Glukhova, G. K. Fukin, S. Dechert, M. Hummert, and H. Schumann, Z. Anorg. Allg. Chem., 2004, 630, 501.

    Article  CAS  Google Scholar 

  24. S. S. Batsanov, Eksperimental’nye osnovy strukturnoi khimii [Experimental Fundamentals of Structural Chemistry], Izd-vo standartov, Moscow, 1986, p. 238 (in Russian).

    Google Scholar 

  25. G. M. Sheldrick, Empirical Absorption Correction Program, Universität Göttingen, Gö ttingen (Germany), 1996.

    Google Scholar 

  26. G. M. Sheldrick, Program for Crystal Structure Solution, Universität Göttingen, Gö ttingen (Germany), 1990.

    Google Scholar 

  27. G. M. Sheldrick, Program for Crystal Structure Refinement, Universität Göttingen, Gö ttingen (Germany), 1997.

    Google Scholar 

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    I. L. Fedushkin, N. M. Khvoinova, A. Yu. Baurin & G. K. Fukin

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  1. I. L. Fedushkin
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  2. N. M. Khvoinova
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  3. A. Yu. Baurin
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  4. G. K. Fukin
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 436–440, March, 2006.

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Fedushkin, I.L., Khvoinova, N.M., Baurin, A.Y. et al. Acenaphthylene-1,2-diamine radical cation. Molecular structure of the [(dpp-BIAN)H2]·+[X]− complex ((dpp-BIAN)H2 is N,N′-bis(2,6-diisopropylphenyl)-acenaphthylene-1,2-diamine; X = Cl or I). Russ Chem Bull 55, 451–456 (2006). https://doi.org/10.1007/s11172-006-0277-0

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  • DOI: https://doi.org/10.1007/s11172-006-0277-0

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