Hydrogen bonding interaction of diphenylbarbituric acid and 9-ethyladenine. Crystal structure of a 1:1 complex

Abstract

There are several different types of adenosine receptors found in the brain and molecules capable of interacting with the adenine ring system may have an effect on brain activity. Phenobarbital and diphenylhydantoin, two commonly used antiepileptic drugs have been shown to form hydrogen bonded complexes with adenine derivatives. Although 5,5-diphenylbarbituric acid has anticonvulsant properties equivalent to phenobarbital, neither its structure nor possible interactions with adenine have been investigated. 5,5-Diphenylbarbituric acid and 9-ethyladenine were, therefore, cocrystallized and the three-dimensional 1:1 hydrogen bonded complex was determined by X-ray diffraction. The crystals are monoclinic, C2/c, a = 28.457(9), b = 10.633(3), c = 13.995(4) Å, β = 100.20(2)°, Z = 8, R = 0.067 for 1680 reflections with I > 3σ(I). The molecules propagate along the b crystallographic axis in an alternating fashion in which adjacent adenine and barbiturate molecules interact through a pair of hydrogen bonds. Two-fold symmetry related barbiturate carbonyl groups in neighboring planes of hydrogen bonded ribbons are involved in dipole–dipole attractive interactions. This hydrogen bonding pattern is compared to patterns found in other barbiturate–adenine complexes.Key words: hydrogen bonding, crystal structure, barbiturates, adenine, anticonvulsants.