Further evidence is presented to show that in all phenols the hydroxyl group is coplanar with the aromatic ring and that in ortho-substituted phenols the hydroxyl group exists in cis-and trans-orientations with respect to the ortho-position. When the ortho-substituent is likely to take part in intramolecular hydrogen bonding the stretching frequency of the trans-hydroxyl group can be related to the substituent constant, as in other phenols.IN Part I the effect of substituents on the formation of intermolecular hydrogen bonding in phenols in the liquid state was described. Since it is now well established that the spectral characteristics of vibrational bands of functional groups attached to an aromatic ring are systematically influenced by the position and nature of other substituents within the ring, the small variations of the free hydroxyl stretching frequencies were not unexpected.Thompson and Steel2 have shown that the frequency and intensity of the cyanogroup stretching vibration in
Dewar a.nd Ptvttnaw: A cid-cratalysed 820. Acid-catalysed Rearrangements of AlEyl Aryl Ethers. Part I1I.l Rearrangements in the Presence of Aluminium Bromide ; the Mechanism of Such, Rearrangements.
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