Abstract
IN the September issue of the Journal of the Chemical Society, Baker and Ingold state that the nitration of benzoic esters is being investigated at Leeds. A similar study is in progress in these laboratories, and preliminary results show, for example, that the proportion of the m-nitrobenzoic acid derivative obtained on nitration rises in the series Ph.CO2←CR3 (R = alkyl), Ph.CO2.CH3, Ph.CO2→CH2→C6H4NO2. This is in accordance with the writer's theoretical views (Chemistry and Industry, 1925, 44, 118, 563; Allan, Oxford, Robinson, and Smith, J. Chem. Soc., 129, 401, 1926; Ing and Robinson, ibid., 1655), and it is anticipated that the nitration of benzoic esters (and of substituted benzamides) will afford a convenient auxiliary method for the estimation of the electron affinities of various groups. The arrows show the assumed direction of displacement of electrons, methyl benzoate being the standard of reference.
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ROBINSON, R. The Influence of General Electron Displacement on the Reactivity of Conjugated Systems in the Molecules of Carbon Compounds. Nature 118, 627 (1926). https://doi.org/10.1038/118627d0
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DOI: https://doi.org/10.1038/118627d0
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