Summary
In an aqueous buffer solution (pH 6...64) p-diazochlorbenzene reacts with 2-naphthol-6,8-disulphonic acid four times faster than with the deuterated compound 1-d-2-naphthol-6, 8-disulphonic acid. This shows that the proton loss is rate determining. Other diazo coupling reactions do not give such a kinetic isotope effect.
References
L. Melander, Arkiv Kemi2, 211 (1950); vgl. Zusammenfassung inC. K. Ingold,Structure and Mechanism in Organic Chemistry (London 1953), S. 279, 301.
U. Berglund-Larsson undL. Melander, Arkiv Kemi6, 219 (1953).
D. Bryce-Smith, V. Gold undD. P. N. Satchell, J. Chem. Soc.1954, 2743.
C. K. Ingold, C. G. Raisin undC. L. Wilson, J. Chem. Soc.1936, 1640.
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Zollinger, H. Kinetische Isotopeneffekte bei elektrophilen aromatischen Substitutionen. Experientia 10, 481–482 (1954). https://doi.org/10.1007/BF02166166
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DOI: https://doi.org/10.1007/BF02166166