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Geometrical and energetical aspects of structure of 3,6-di-tert-butyl-o-benzoquinones

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Abstract

From the geometrical point of view, all observed conformations of the 3,6-di-tert-butyl-o-benzoquinone fragments are determined by the inequivalent positions of the Me groups of the tBu substitutes relative to the carbonyl oxygen atoms. The geometrical inequivalence is believed to cause the energetic inequivalence of the Me groups. The relevant quantum mechanical computations revealed intramolecular contacts of the C=O···H-(tBu)-type (2.37–3.83 kcal/mole) that can be interpreted to be hydrogen bonding interactions.

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References

  1. Cortlandt G, Pierpont CG, Buchanan RM (1981) Coord Chem Rev 38:45

    Article  Google Scholar 

  2. Pierpont CG (2001) Coord Chem Rev 216:99

    Article  Google Scholar 

  3. Pierpont CG (2001) Coord Chem Rev 219:415

    Article  Google Scholar 

  4. Hendrickson DN, Pierpont CG (2004) Top Curr Chem 234:63

    CAS  Google Scholar 

  5. Cherkasov VK, Abakumov GA, Grunova EV, Poddel’sky AI, Fukin GK, Baranov EV, Kurskii YA, Abakumova LG (2006) Chem Eur J 12:3916

    Article  CAS  Google Scholar 

  6. Abakumov GA, Cherkasov VK, Grunova EV, Poddel’sky AI, Abakumova LG, Kurskii YA, Fukin GK, Baranov EV (2005) Doklady Chem 405(2):222

    Article  CAS  Google Scholar 

  7. Abakumov GA, Poddel’sky AI, Grunova EV, Cherkasov VK, Fukin GK, Kurskii YA, Abakumova LG (2005) Angew Chem Int Ed 44:2767

    Article  CAS  Google Scholar 

  8. Kuropatov VA, Cherkasov VK, Kurskii YA, Fukin GK, Abakumova LG, Abakumov GA (2006) Russ Chem Bull Int Ed 4:708

    Article  Google Scholar 

  9. Abakumov GA, Cherkasov VK, Kocherova TN, Druzkov NO, Kurskii YA, Bubnov MP, Fukin GK, Abakumova LG (2007) Russ Chem Bull Int Ed 9:1849

    Article  Google Scholar 

  10. Prokof’eva TI, Vol’eva VB, Prokof’ev AI, Belostotskaya S, Komissarov NL, Ershov VV (2000) Chem Heterocycl Compd 36(8):923

    Article  Google Scholar 

  11. Bader RFW (1990) Atoms in molecules—a quantum theory. Oxford University Press, Oxford

    Google Scholar 

  12. Keith TA (2008) AIMAll

  13. Popelier PLA (1998) J Phys Chem A 102:1873

    Article  CAS  Google Scholar 

  14. Koch U, Popelier PLA (1995) J Phys Chem 99:9747

    Article  CAS  Google Scholar 

  15. Espinosa E, Molins E, Lecomte C (1998) Chem Phys Lett 285:170

    Article  CAS  Google Scholar 

  16. Zefirov YV, Zorkii PM (1995) Russ Chem Rev 64:446

    Article  CAS  Google Scholar 

  17. Garnov VA, Nevodchikov VI, Abakumov GA, Abakumova LG, Kurskii YA, Cherkasov VK (1985) Bull Akad Sci USSR Div Chem Sci 34:2589

    Article  Google Scholar 

  18. Abakumov GA, Cherkasov VK, Abakumova LG, Nevodchikov VI (1990) Bull Akad Sci USSR Div Chem Sci 39(5):984

    Article  Google Scholar 

  19. Abakumov GA, Cherkasov VK, Abakumova LG, Nevodchicov VI, Druzhkov NO, Makarenko NP, Kursky YA (1995) J Organometal Chem 491:127

    Article  CAS  Google Scholar 

  20. Abakumov GA, Cherkasov VK, Abakumova LG, Druzhkov NO, Nevodchicov VI, Kursky YA, Makarenko NP (1991) Organomet Chem USSR 4:683

    Google Scholar 

  21. Garnov VA, Nevodchikov VI, Abakumova LG, Abakumov GA, Cherkasov VK (1987) Bull Akad Sci USSR Div Chem Sci 36(8):1728

    Article  Google Scholar 

  22. Gordon J, Ford A (1972) The chemist’s companion. Wiley, New York

    Google Scholar 

  23. Bruker (2000) SAINTPlus data reduction and correction program v. 6.02a, Bruker AXS. Madison, Wisconsin, USA

    Google Scholar 

  24. Sheldrick GM (1998) SADABS v.2.01, Bruker/Siemens area detector absorption correction program, Bruker AXS. Madison, Wisconsin, USA

    Google Scholar 

  25. Sheldrick GM (2000) SHELXTL v. 6.12, Structure determination software suite, Bruker AXS. Madison, Wisconsin, USA

    Google Scholar 

  26. Granovsky AA (2009) Firefly (PC GAMESS) 7.1.C

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Acknowledgments

This work was supported by NSh 4182.2008.3; NSh 3826.2010.3, Russian Foundation for Basic Research (Project Nos. 09-03-97034-r_povolzh’e_a, 07-03-00711, 07-03-00819, 08-03-12090-ofi, 08-03-97055-r_povolzh’e_a).

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Authors and Affiliations

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

    G. K. Fukin, A. V. Cherkasov, M. P. Shurygina, N. O. Druzhkov, V. A. Kuropatov, S. A. Chesnokov & G. A. Abakumov

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  1. G. K. Fukin
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  2. A. V. Cherkasov
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  3. M. P. Shurygina
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  4. N. O. Druzhkov
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  5. V. A. Kuropatov
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  6. S. A. Chesnokov
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  7. G. A. Abakumov
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Correspondence to G. K. Fukin.

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Fukin, G.K., Cherkasov, A.V., Shurygina, M.P. et al. Geometrical and energetical aspects of structure of 3,6-di-tert-butyl-o-benzoquinones. Struct Chem 21, 607–611 (2010). https://doi.org/10.1007/s11224-010-9590-1

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  • DOI: https://doi.org/10.1007/s11224-010-9590-1

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