Abstract
Infrared spectra of the title compounds were studied in the 1500–4000 cm −1 region. N-H — N hydrogen bonding was found to occur in crystalline 1,4,8,11-tetra- azacyclotetradecane (I) and in its 5,12-dimethyl derivatives (IIA and IIB), whereas no association was detected in saturated solutions of all compounds in molten amine I and in its crystalline 5,7,7,12, 14,14-hexamethyl derivative (IIIA). These facts are interpreted as induction of hydrogen bonding by crystal-lattice forces. It proved impossible to establish either the intra- or the intermolecular character of the observed hydrogen bonding. A group of bands in the 2600–2800 cm −1 region is assigned to the trans-CH. bands and their origin is interpreted on the basis of a diamond lattice conformation I (c) proposed for the tetra- azacyclotetradecane ring.
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