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Chemistry. 2005 Feb 18;11(5):1459-66.

Steric control over hydrogen bonding in crystalline organic solids: a structural study of N,N'-dialkylthioureas.

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Chemical Sciences Division, Oak Ridge National Laboratory, P.O. Box 2008, MS-6119, Oak Ridge, TN 37831-6119, USA.


Hydrogen bonding in crystalline N,N'-dialkylthioureas was examined with the help of single-crystal X-ray diffraction, DFT calculations, and Cambridge Structural Database (CSD) analysis. A CSD survey indicated that unlike the related urea derivatives, which persistently self-assemble into one-dimensional hydrogen-bonded chains, the analogous thioureas can form two different hydrogen-bonding motifs in the solid state: chains, structurally similar with those found in ureas, and dimers, that further associate into hydrogen-bonded layers. The formation of one motif or another can be manipulated by the bulkiness of the organic substituents on the thiourea group, which provides a clear example of steric control over the hydrogen bonding arrangement in crystalline organic solids.


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