Manipulation of an intramolecular NH center dot center dot center dot O hydrogen bond by photoswitching between stable E/Z isomers of the cinnamate framework

作者：Matsuhira Takashi; Yamamoto Hitoshi^*; Okamura Taka Aki; Ueyama Norikazu

来源：Organic and Biomolecular Chemistry, 2008, 6(11): 1926-1933.

DOI：10.1039/b719960k

Novel carboxylic acid derivatives were synthesized, which allowed switching of the intramolecular distance between amide group and carboxylic oxygen atoms using E to Z photoisomerization of the cinnamate framework. An intramolecular NH center dot center dot center dot O hydrogen bond was formed in the Z carboxylate compound not only in solution but also in the solid state. The pK(a) value of the carboxylic acid was lowered as a consequence of the E/Z photoisomerization.

• 出版日期2008