Issue 11, 2008
From the journal:

Organic & Biomolecular Chemistry

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

Takashi Matsuhira,a   Hitoshi Yamamoto,*a   Taka-aki Okamuraa  and  Norikazu Ueyamab  

* Corresponding authors

a Department of Macromolecular Science, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan
E-mail: jin@chem.sci.osaka-u.ac.jp
Fax: +81-6-6850-5474
Tel: +81-6-6850-5451

b Center for Advanced Science and Innovation, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
Fax: +81-6-6879-7796
Tel: +81-6-6979-7795

Abstract

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

Graphical abstract: Manipulation of an intramolecular NH⋯O hydrogen bond by photoswitching between stable E/Z isomers of the cinnamate framework

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Article information

DOI
https://doi.org/10.1039/B719960K
Article type
Paper
Submitted
02 Jan 2008
Accepted
21 Feb 2008
First published
08 Apr 2008

Org. Biomol. Chem., 2008,6, 1926-1933

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

T. Matsuhira, H. Yamamoto, T. Okamura and N. Ueyama, Org. Biomol. Chem., 2008, 6, 1926 DOI: 10.1039/B719960K

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