Skip to main content
Log in

Anthraquinone and anthrone series

Part XI. Steric hindrance in dibenzanthronyls and dibenzanthrones

  • Published:
Proceedings of the Indian Academy of Sciences - Section A Aims and scope Submit manuscript

Summary

The absorption spectra of dibenzanthrone, 16: 17-dihydroxydibenzanthrone, 16: 17-and 3: 12-dimethoxydibenzanthrone have been determined ino-chlorophenol. The bathochromic shift of the dibenzanthrone spectrum on substitution of two methoxyl groups in the 16: 17-positions of dibenzanthrone is ascribed to the over-riding tendency of the dibenzanthrone ring system to remain planar and hence force the methoxyl groups also to be coplanar with the ring system.

The absorption spectra of 3:3′- and 4:4′-dibenzanthronyls have been reported and discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Brookeret al., Chem. Revs., 1947,41, 325;cf. Ferguson,Ibid., 1948,43, 385; Braudeet al., J. Chem. Soc., 1949, 1890.

    Article  Google Scholar 

  2. Remick,Electronic Interpretations of Organic Chemistry, Wiley, New York, 2nd Ed., 1949, p. 323.

    Google Scholar 

  3. J. Am. Chem. Soc., 1940,62, 2906.

  4. Ibid., 1945,67, 1838;cf. Grammaticakis,Bull. Soc. Chim., 1949,134, 761.

  5. J. Am. Chem. Soc., 1949,71, 1714.

  6. Picketet al., Ibid., 1936,58, 2296; 1950, 72, 44.

    Article  Google Scholar 

  7. Ley and Pfeiffer,Ber., 1921,54, 363.

    Google Scholar 

  8. Calvin,J. Org. Chem., 1939,4, 256; Sherwood and CalvinJ. Am. Chem. Soc., 1942,64, 1350; see also Lewis and Calvin,Chem. Revs., 1939,25, 273.

    Article  Google Scholar 

  9. Pestemer and Mayer-Pitsch,Monatsh., 1937,70, 104.

    Article  Google Scholar 

  10. Twielacker and Ozegowski,Ber., 1940,73, 893.

    Google Scholar 

  11. Rodebushet al., J. Am. Chem. Soc., 1940,62, 2906; 1941,63, 3019; 1946,68, 896.

    Article  Google Scholar 

  12. Westheimer and Mayer,J. Chem. Phys., 1946,14, 733; Hill,Ibid., 465.

    Article  Google Scholar 

  13. Brode and Morris,J. Am. Chem. Soc., 1948,70, 2485;J. Org. Chem., 1948,13, 207.

    Article  Google Scholar 

  14. Blout and Gofstein,J. Am. Chem. Soc., 1945,67, 13; see also Leonardet al., Ibid., 1950,72, 484, 5388.

    Article  Google Scholar 

  15. Ibid., 1948,70, 199.

  16. Jones, Ibid., 1941,63, 1658; 1945,67, 2127; Hirshberg,Trans. Faraday Soc., 1948,44, 285.

    Article  Google Scholar 

  17. Z. physik. Chem., 1951,155A, 353;cf. Alberman,J. Chem. Soc., 1952, 3284; Beale and Roe,J. Amer. Chem. Soc., 1952,74, 2302.

  18. Robertson,Proc. Roy. Soc., 1935,150A, 348.

    Google Scholar 

  19. See also Weigand and Merkel,Ann., 1947,557, 242.

    Google Scholar 

  20. Cook, Jones and Polya,J. Chem. Soc., 1939, 1315.

  21. Zechmeister,Chem. Revs., 1944,34, 267.

    Article  Google Scholar 

  22. J. Am. Chem. Soc., 1942,64, 593.

  23. Jones, Ibid., 1943,65, 1815.

    Article  Google Scholar 

  24. Ibid., 1941,63, 3252.

  25. Jones, Ibid., 1941,63, 313; see also Jones,Chem. Revs., 1943.32, 1.

    Article  Google Scholar 

  26. J. Am. Chem. Soc., 1940,62, 2295.

  27. Friedel and Orchin,Ultraviolet spectra of Aromatic Compounds, Wiley, New York, 1951.

    Google Scholar 

  28. P. N. Pandit,Ph.D. Thesis, University of Bombay, 1952.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Padhye, M.R., Rao, N.R. & Venkataraman, K. Anthraquinone and anthrone series. Proc. Indian Acad. Sci. (Math. Sci.) 38, 307–319 (1953). https://doi.org/10.1007/BF03045259

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03045259

Keywords

Navigation