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Open Access Crystal structure of 2,4,6-trimethylbenzoic anhydride

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The title compound, C20H22O3, was formed in the reaction between 2,4,6-trimethylbenzoic acid and N,N-diisopropylethylamine in the presence of 1,3-dichloro-1,3-bis(dimethylamino)propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusively alkyl-substituted benzoic anhydride to have been structurally characterized. The asymmetric unit consists of a half molecule, the other half of which is generated by twofold rotation symmetry; the dihedral angle between the symmetry-related aromatic rings is 54.97 (3)°. The geometric parameters of the aromatic ring are typical of those for 2,4,6-trimethylphenyl substituted groups. The C=O and C—O bond lengths are 1.1934 (12) and 1.3958 (11) Å, respectively, and the angle between these three atoms (O=C—O) is 121.24 (9)°. In the crystal, molecules are linked by weak C—H...O hydrogen bonds and C—H...π interactions. The packing features wavy chains that extend parallel to [001].
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Document Type: Research Article

Affiliations: Atlantic Centre for Green Chemistry, Department of Chemistry, Saint Mary's University, 923 Robie Street, Halifax, Nova Scotia, B3H 3C3 Canada

Publication date: January 1, 2017

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