Relation Between Structure and Mesogenic Activity in α,α′-Dimethylbenzalazines Influence of Intramolecular H-Bonding (II)

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Abstract
The central molecular geometry of three series of benzalazines: 4,4′-Dialkoxy-α,α′-Dimethylbenzalazines, 4,4′-dialkoxy-2,2′-dihydroxy-α,α′-Dimethylbenzalazines, and 4,4′-dialkoxy-2-hydroxy-α,α′-Dimethylbenzalazines was studied by U.V., I.R., and 1H.N.M.R. spectroscopy. All the compounds studied show the E-E configuration. The intramolecular H-bond between the nitrogen of the azine central group and the H of the OH group in position 2 of the aromatic ring is “exceptionally” strong in accordance with the calculations made using Schaefer's equation. This bond conditions the geometry of the molecules, as well as their mesogenic properties. The intramolecular H-bonding favors the formation of mesophases whose properties are also related to the number of bonds of this type which the molecules contain.

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