Abstract
INFORMATION about the effect of the aromatically bonded sulphonic group has been obtained by studying its influence on the reactivity of other substituents of the same molecule. A suitable way is the measurement of acidity constants of phenols, anilinium ions and aromatic carbonic acids. Earlier investigations on these constants for naphthylaminesulphonic acids1 and naphtholsulphonic acids2 showed the existence of an electrostatic effect which is due to the dipolar structure and the negative charge of the SO3− substituent. A. Bryson, who investigated the naphthylamines, points out that the differences in the pK-values provide evidence for the conjugative interaction of the sulphonate ion and the aromatic ring. I was unable to extend this conclusion to the naphtholsulphonic acids.
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References
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ZOLLINGER, H. Mesomeric Effect of the Sulphonic Acid Group. Nature 172, 257–258 (1953). https://doi.org/10.1038/172257b0
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DOI: https://doi.org/10.1038/172257b0
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