Modeling the Self-Assembly of 5-Hydroxy-6-methyluracil within Electrostatic Potential Approach

The sites of reactions in 5-hydroxy-6-methyluracil (HMU) and its dimeric and tetrameric associates are studied theoretically in terms of the electrostatic potential (ESP). The ESP approach allows us to construct the most stable combinations of HMU associates and to study HMU self-assembly without simulating all possible associates. A self-assembly scheme is proposed for HMU. N1–H···O1 bonds initially form between the molecules. If the first recognition center (RC) is occupied, N3–H···O2 bonds form with the participation of the third RC. The resulting ribbons with alternating contacts 1–1 and 3–3 are cross-linked through the electrostatic attraction of hydroxyl groups and the forces of dispersion between methyl groups.