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The supramolecular behaviour of adenine with succinic, fumaric and maleic acids; tautomerism, cocrystallisation, salt formation and solvation

DOI: 10.1021/cg301561j DOI Help

Authors: Laura Thompson (University of Birmingham) , Norhanida Elias (University of Birmingham) , Louise Male (University of Birmingham) , Maryjane Tremayne (University of Birmingham)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Crystal Growth & Design , VOL 13 (4)

State: Published (Approved)
Published: February 2013

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 (1), anhydrous salts with fumaric acid (2) and maleic acid (3), and a methanolated salt with maleic acid (4). 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 (3) enables the stabilization of the unusual 3H,7H adeninium tautomer within a purely molecular material.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 18/02/2013 12:24

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