Supramolecular Behavior of Adenine with Succinic,
Fumaric, and Maleic Acids: Tautomerism, Cocrystallization, Salt Formation,
and Solvation
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Abstract
The powerful hydrogen bonding capability
of adenine makes it a
key component of the DNA double helix, while as a crystalline molecular
material, these hydrogen bond donors and acceptors make it a good
potential cocrystal component possessing distinct physical properties.
Here, we report the preparation and structure determination of four
adenine-based multicomponent adducts formed with a number of dicarboxylic
acids: an anhydrous cocrystal with succinic acid (<b>1</b>),
anhydrous salts with fumaric acid (<b>2</b>) and maleic acid
(<b>3</b>), and a methanolated salt with maleic acid (<b>4</b>). The supramolecular behavior of adenine in these materials
is discussed in terms of strong hydrogen-bonded bidentate motifs formed
between the adenine and acid components and the homomeric adenine
synthons retained in these structures. The additional formation of
a CH···N interaction on the Watson–Crick site
in (<b>3</b>) enables the stabilization of the unusual 3<i>H</i>,7<i>H</i> adeninium tautomer within a purely
molecular material