Use of Hydrogen Bonds To Control Molecular Aggregation. Behavior of Dipyridones and Pyridone-Pyrimidones Designed To Form Cyclic Triplexes

Article abstract of DOI:10.1021/jo00110a050

The tendency of 2-pyridones and related heterocycles to form cyclic hydrogen-bonded dimers allows them to be used as sticky sites that induce molecules in which they are incorporated to associate in particular ways.Compound 7, which is constructed from pyridone and pyrimidone subunits linked to a rigid linear acetylenic spacer, incorporates an array of hydrogen-bonding sites designed to favor the formation of a cyclic triplex.Pyridone-pyrimidone 7 was synthesized and the structure of its DMSO solvate was determined by X-ray crystallography.Aggregation does not produce a cyclic triplex but rather gives chains in which adjacent molecules of compound 7 are linked by single hydrogen bonds.