The chemical shift of the NH protons for a series of monomethyl-, dimethyl- and trimethyl- substituted 2- and 4- quinolones has been studied. Compounds with an 8-methyl substituent exhibit a characteristic upfield shift which is considered to be due to a reduction in hydrogen bonding as a result of steric effects. The application of this effect to the identification of alkyl substituted quinolones and some natural products is discussed.
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Claret et al. (1974) studied this question.
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