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Mesomerism and Orientation
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  • Letter
  • Published: 02 September 1939

Mesomerism and Orientation

  • G. BADDELEY1 

Nature volume 144, page 444 (1939)Cite this article

  • 431 Accesses

  • 12 Citations

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Abstract

THE brief reference to the apparently anomalous nitration of the acetyl derivative of 2-m-xylidine to a 4-nitro derivative and its interpretation in the paper just published by Ingham and Hampson1 makes it desirable to point out that many of the anomalies associated with ortho-substituents (and usually grouped under the heading of ‘ortho effects’) find their explanation in the steric hindrance of resonance discussed by Ingham and Hampson. This view had been arrived at independently in connexion with a systematic study of isomerizations produced by aluminium chloride2. It is hoped to publish an account of the further development of this work in the near future, but meanwhile the following selected illustrations of the more general application of this view may be cited.

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References

  1. Ingham and Hampson, J. Chem. Soc., 981 (1939).

  2. Compare Kenner and Baddeley, J. Chem Soc., 303 (1935).

  3. v. Braun, Ber., 49, 1101; 51, 252.

  4. Davies and Addis, J. Chem. Soc., 1622 (1927).

  5. Davis, J. Chem. Soc., 1397 (1909); Z. phys. Chem., 353, 369 (1912).

  6. Dippy, Evans, Gordon, Lèwis and Watson, J. Chem. Soc., 1421 (1937).

  7. McKenzie, J. Chem. Soc., 1135 (1901).

  8. Norris, Z. phys. Chem., 101, 333 (1921).

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  9. Olivier et al., Rec trav. chem., 1922–1926.

  10. Branch, Yabroff and Bettmann, J. Amer. Chem. Soc., 56, 937, 1865 (1934).

    Article  CAS  Google Scholar 

  11. Boyd et al., J. Chem. Soc., 105, 2117 (1914); 115, 1239 (1919). Burkhardt et al., J. Chem. Soc., 17 (1936).

    Article  CAS  Google Scholar 

  12. Meyer, V., Ber., 28, 3213; 29, 848, 2564.

  13. Short and Hill, J. Chem. Soc., 1123 (1935).

  14. Klages, Ber., 37, 1715.

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Author information

Authors and Affiliations

  1. College of Technology, Manchester

    G. BADDELEY

Authors
  1. G. BADDELEY
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BADDELEY, G. Mesomerism and Orientation. Nature 144, 444 (1939). https://doi.org/10.1038/144444a0

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  • Issue date: 02 September 1939

  • DOI: https://doi.org/10.1038/144444a0

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