Abstract
The tetrabutylammonium, Li+ and Na+ complexes of six N-(1,6-dihydro-6-oxopyrimidin-2-yl) amino acids (CAA) were studied by FTIR spectroscopy and compared with results obtained earlier with isomeric amino acids. In all amino acids an intramolecular OH⋯ON ⇌ O–⋯H+ON hydrogen bond with large proton polarizability has been observed. In the tetrabutylammonium salts of the amino acids the carboxylic acid group forms a strong asymmetrical NH⋯O– bond. In all Li+ compounds intramolecular Li+ bonds with double-minimum proton potentials and large ‘Li+ polarizability’ are found. In the case of the Na+ bonds flat, single-minimum Na+ potentials are present in the intramolecular Na+ bonds. The amplitude of the fluctuation, and hence the ‘Na+ polarizability’, is however small owing to the large mass of the Na+ ions.
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