Supramolecular Behavior of Adenine with Succinic, Fumaric, and Maleic Acids: Tautomerism, Cocrystallization, Salt Formation, and Solvation

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

Supramolecular Behavior of Adenine with Succinic, Fumaric, and Maleic Acids: Tautomerism, Cocrystallization, Salt Formation, and Solvation

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

Supramolecular Behavior of Adenine with Succinic, Fumaric, and Maleic Acids: Tautomerism, Cocrystallization, Salt Formation, and Solvation

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

Supramolecular Behavior of Adenine with Succinic, Fumaric, and Maleic Acids: Tautomerism, Cocrystallization, Salt Formation, and Solvation

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