Letter | Published:

Orienting Power of the Nitroso-Group and the Formula of Nitrosobenzene

Nature volume 130, pages 400401 (10 September 1932) | Download Citation

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Abstract

THE nitroso-group in an aromatic nitroso compound appears to be chemically abnormal. Thus, in the case of nitrosobenzene, failure 1 to prepare salts or coordination compounds in which the nitroso-nitrogen acts as a donor atom, shows the accepted formula (1), with a tercovalent nitrogen atom, to be incorrect. Equality of the value of the dipole moment for this substance with that for nitrobenzene would indicate (2) as a possible formula, in which case the nitroso-group should be meta-directing in aromatic substitution reactions.

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References

  1. 1.

    Unpublished experiments.

  2. 2.

    , , and , Ber., 31, 1513; 1898.

  3. 3.

    , J.C.S., 516; 1925: and , Ber., 30, 512; 1897.

  4. 4.

    , loc. cit.

  5. 5.

    , Dissert., Zurich, 29; 1904.

  6. 6.

    , J.C.S., 810; 1931.

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    and , J.C.S., 2363; 1930.

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    , "Die Hydrazine", Stuttgart, 71; 1913.

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    , J. Amer. Chem. Soc., 53, 3234; 1931.

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Author information

Affiliations

  1. The Ralph Forster Laboratories of Organic Chemistry, University College, London, W.C.1.

    • R. J. W. LE FÈVRE

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  1. Search for R. J. W. LE FÈVRE in:

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DOI

https://doi.org/10.1038/130400a0

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