Journal
TETRAHEDRON LETTERS
Volume 50, Issue 3, Pages 320-324Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.11.002
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Funding
- Natural Science Foundation of China [20732007, 20621062, 20425208, 20572126, 20672137]
- National Basic Research Project [2007CB808000]
- Chinese Academy of Sciences
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The capacity of sulfur to form intramolecular five- or six-membered S center dot center dot center dot H-N hydrogen bonding in aromatic amides is assessed. The five-membered S center dot center dot center dot H-N hydrogen bonding is observed in crystal structures of five compounds, whereas the six-membered S center dot center dot center dot H-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=O center dot center dot center dot H-N hydrogen bonding. (2D) H-1 NMR experiments indicate that both patterns also exist in chloroform. (C) 2008 Elsevier Ltd. All rights reserved.
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