Influence of the Structure of Ketones and Acidity of Phenols Upon Their Complexation Processes. Part 2. n‐ vs. π‐Complex Competition Depending on Ketone Branching and Phenol Acidity.
1991
Abstract For phenol-alkylketone associations, lineshape analysis of the associated ν OH band allows for the separation of two different complexes attributed either to π or n (lone-pair) carbonyl electrons. Using an original methodology, individual constants K n and K π have been evaluated and their evolution according to the structure of the two partners (ketone and phenol) characterized by a factor analysis treatment. For n -complexes, reduced ketone characteristics K nc are proportional to the number of branches alpha to the carbonyl, K π being insensitive to the structure of the ketone. Both K n and K π are linearly related to the phenol acidity, but with different sensitivities. This induces striking differences in the relative weight of the n - and π-complexes depending on the ketone-phenol pair investigated. For ortho -halogenophenols, the influence of intramolecular hydrogen bonding is discussed.
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