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Intramolecular hydrogen bonding occurring in o-nitrophenol is discussed with special reference to the effects of the steric interactions on the absorption bands and on the bonding. An alkyl substituent vicinal to the OH group, or a methyl group vicinal to the NO 2  group appears to strengthen the intramolecular hydrogen bond in o-nitrophenol. The O—H vibrational stretching frequency in o-nitrophenol appears to be more susceptible to steric than to mesomeric interactions, and a methyl substituent vicinal to the nitro group in o-nitrophenols is found to give rise to a characteristic O—H stretching vibration band. For 6-t-butyl-2-nitrophenol, a special, "protected" hydrogen bond is postulated. In some of the o-nitrophenols, intermolecular hydrogen bonding gives rise to appreciable ultraviolet intensity decreases presumably because of increased steric interactions.

canadian journal of chemistry

THE STUDY OF HYDROGEN BONDING AND RELATED PHENOMENA BY ULTRAVIOLET LIGHT ABSORPTION: PART VI. THE EFFECT OF STERIC INTERACTIONS ON THE INTRAMOLECULAR HYDROGEN BOND IN <i>o</i>-NITROPHENOL

THE STUDY OF HYDROGEN BONDING AND RELATED PHENOMENA BY ULTRAVIOLET LIGHT ABSORPTION: PART VI. THE EFFECT OF STERIC INTERACTIONS ON THE INTRAMOLECULAR HYDROGEN BOND IN o-NITROPHENOL