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The structure of the π-molecular complex between 1,4-dihydro-9,10-anthrahydroquinone and 1,4-dihydro-9,10-anthraquinone

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Abstract

The structure of the π-molecular complex (10) was assigned on the basis of the solid state13C-nmr spectrum. The solid state13C-nmr spectrum of quinhydrone (12) has also been determined. Accurate1H and13C chemical shift assignments have been made for the compounds3,5,6,7,8, and10 on the basis of HMQC and HMBC spectral data. The π-molecular complex10 crystallizes in the space groupP21 In with cell parameters:a=4.052 (1) Å,b=6.477 (1) Å,c=19.093 (2) Å, β=90.17 (1)o,z=1,D c =1.400 g mc−32. Crystal and molecular structure of the title compound, C28H22O4, has been determined by an X-ray analysis of10 by direct methods from diffractometer data and refined by full-matrix least-squares

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References

  1. Joshi, B.S.; Gawad, D.H.; Pelletier, S.W.; Kartha, G.; Bhandary, K.Tetrahedron Lett. 1984,25, 5847–5850.

    Article  CAS  Google Scholar 

  2. Joshi, B.S.; Jiang, Q.P.; Rho, T.K.; Pelletier, S.W.J. Org. Chem. 1994,59, 8220–8232; Jiang, Q.P.; Joshi, B.S.; Pelletier, S.W.Tetrahedron Lett. 1991,32, 5283–5286.

    Article  CAS  Google Scholar 

  3. Diels, O.; Alder, K.Liebigs Ann. Chem. 1928,460, 98–122

    CAS  Google Scholar 

  4. Grinev, A.N.; Terent'ev, A.P.Zhur Obshchei. Khim. 1958,28, 75–78 (Chem. Abstr. 1958,52, 12830h).

    CAS  Google Scholar 

  5. Diels, O.; Alder, K.Ber. 1929,62B, 2337–2372.

    CAS  Google Scholar 

  6. Zollinger, Hch.Helv. Chim. Acta 1961,44, 1211.

    Article  Google Scholar 

  7. Pelletier, S.W.; Chokshi, H.P.; Desai, H.K.J. Nat. Prod. 1986,49, 892.

    Article  CAS  Google Scholar 

  8. teXsan: Single Crystal Structure Software, Version 1.7.1, Molecular Structure Corporation. The Woodlands, TX,1995, 77381.

  9. Joshi, B.S.Chem. Ind. 1957, 525; Kharasch, M.S.; Joshi, B.S.J. Org. Chem. 1957,22, 1439.

    Google Scholar 

  10. Lonsdale, K.; Milledge, H.J.; Sayed, K.E.Acta Crystallogr. 1966,20, 1.

    Article  CAS  Google Scholar 

  11. (a)Heilbron'sDictionary of Organic Compounds (1965) p. 1049;

  12. Grandmougin,Ber.,1906,39, 3563; Meyer.Liebigs Ann. Chem. 1911,379, 3563.

    Google Scholar 

  13. Dimmel, D.R.; Shepard, D.J. Org. Chem. 1982,47, 22–29.

    Article  CAS  Google Scholar 

  14. Sakurai, T.Acta Crystallogr. 1968,B24, 403; Sakurai,Acta Crystallogr. 1965,19, 320.

    Google Scholar 

  15. Murthy, B.V.Z. Krystallogr. 1960,113, 445; A.T.H. Lenstra and J.F.J. Van Loock,Bull. Soc. Chem. Belg. 1984,93, 1053.

    Article  Google Scholar 

  16. Heltzel, C.E.; Gunatilaka, A.A.L.; Glass, T.E.; Kingston, D.G.I.Tetrahedron,1993,49, 6757–6762.

    Article  CAS  Google Scholar 

  17. Casey, M.L.; Paulick, R.C.; Whitlock, H.W.J. Org. Chem. 1978,43, 1627–1634.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Natural Products Research, Chemistry Building, The University of Georgia, 90602-2556, Athens, Georgia

    Balawant S. Joshi

  2. Institute for Natural Products Research and Department of Chemistry, The University of Georgia, 30602-2556, Athens, Georgia

    Taikyun Rho & S. William Pelletier

  3. Department of Chemistry, The University of Akron, Akron, Ohio 44325-3601

    Peter L. Rinaldi, Weixia Liu & Todd A. Wagler

  4. X-Ray Diffraction Laboratory, Department of Chemistry, The University of Georgia, 30602-2556, Athens, Georgia

    M. Gary Newton & Doowon Lee

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  1. Balawant S. Joshi
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  2. Taikyun Rho
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  3. Peter L. Rinaldi
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  4. Weixia Liu
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  5. Todd A. Wagler
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  6. M. Gary Newton
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  7. Doowon Lee
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  8. S. William Pelletier
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Joshi, B.S., Rho, T., Rinaldi, P.L. et al. The structure of the π-molecular complex between 1,4-dihydro-9,10-anthrahydroquinone and 1,4-dihydro-9,10-anthraquinone. J Chem Crystallogr 27, 553–559 (1997). https://doi.org/10.1007/BF02576447

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  • DOI: https://doi.org/10.1007/BF02576447

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