Resonance assisted hydrogen bonds (RAHBs) are among the strongest forms of hydrogen bonding known to occur and are found in specific intramolecular hydrogen-bonding systems. Two series of ortho-acylnaphthols were synthesized, as in the figure below, where X or Y = CH3O, CH3, H, Br, Cl, NO2. One series was substituted on the 4-naphthol position (Y), and the other substituted on the 4-benzoyl position (X). A Hammett study was carried out using 1H NMR and 13C NMR to determine the nature of the electronic effects on the internal hydrogen bond in this system. The OH exhibited 1H NMR shifts higher than 13ppm in these compounds.

Hammett study of a resonance assisted hydrogen bond

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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