Hydrogen bonding in salicylic acid increases its acidity
Intramolecular hydrogen bonding in salicylic acid stabilizes the conjugate base and increases its overall acidity compared to non-chelated analogs.
The retrieved literature (specifically papers [0] and [2]) confirms the chemical principle that intramolecular hydrogen bonding in salicylic acid plays a critical role in determining its ionization constants and acidity.
G. E. Dunn, Fei-lin Kung. EFFECT OF INTRAMOLECULAR HYDROGEN BONDING ON IONIZATION CONSTANTS OF SUBSTITUTED SALICYLIC ACIDS. 1966. https://doi.org/10.1139/v66-188
Analyzes the ionization constants of substituted salicylic acids, confirming intramolecular hydrogen bonding effects within the chelate ring structure.
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G. E. Dunn, Thomas L. Penner. Effect of intramolecular hydrogen bonding on the relative acidities of substituted salicylic acids in benzene solution. 1967. https://doi.org/10.1139/v67-274
Discusses how intramolecular hydrogen bonding influences the relative acidities of substituted salicylic acids in solution.
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