Five- and six-membered N–H⋯S hydrogen bonding in aromatic amides

✍ Scribed by Ping Du; X-Kui Jiang; Zhan-Ting Li

• Book ID: 104096002
• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 492 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.11.002

✦ Synopsis

The capacity of sulfur to form intramolecular five-or six-membered SÁ Á ÁH-N hydrogen bonding in aromatic amides is assessed. The five-membered SÁ Á ÁH-N hydrogen bonding is observed in crystal structures of five compounds, whereas the six-membered SÁ Á ÁH-N hydrogen bonding is revealed in crystal structures of three compounds. The trityl group has been used to promote formation of the weak hydrogen bonding because it efficiently inhibits the competition of the intermolecular C@OÁ Á ÁH-N hydrogen bonding. (2D) 1 H NMR experiments indicate that both patterns also exist in chloroform.