Liu Wen-Xia, Jiang Yun-Bao
Department of Chemistry, College of Chemistry and Chemical Engineering, and The MOE Key Laboratory of Analytical Sciences, Xiamen University, Xiamen 361005, China.
J Org Chem. 2008 Feb 1;73(3):1124-7. doi: 10.1021/jo702159r. Epub 2007 Dec 21.
N-(p-Dimethylamino)benzoyl-N'-phenylthiourea as an N-acylthiourea is known to be unable to bind anions due to a strong intramolecular hydrogen bond (IHB). We show here that by inserting an amido group in the N'-phenyl side the newly designed N-benzamido-N'-benzoylthioureas, despite this IHB too, bind strongly to anions with binding constants on the order of 10(6)-10(7) mol(-1) L. Results suggest that potential anion receptors or organocatalysts could be developed on the basis of this framework with a wide structural diversity.
