Abstract
The intramolecularly hydrogen bonded OH group sterically alters the spacial distance between the sites of solute-solvent interaction, and the larger spacial distance causes a weaker solute-sovent interaction. Intramolecular hydrogen bonding also causes the carbonyl group to be relatively less basic which decreases the strength of an intermolecular hydrogen bond formed between the solute and the acidic proton of the solvent. Therefore, there is a smaller vC=O · · · HO frequency decrease compared to vC=O for similar compounds not intramolecularly hydrogen bonded in going from solution in CCl 4 to solution in CHCl 3, or (CH 3) 2SO.
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