Issue 7, 2006
From the journal:

Organic & Biomolecular Chemistry

Photoinduced switching of intramolecular hydrogen bond between amide NH and carboxyl oxygen†

Takashi Matsuhira,a   Hitoshi Yamamoto,*a   Akira Onoda,b   Taka-aki Okamuraa  and  Norikazu Ueyamac  

* 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 Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku, Tokyo 162-8601, Japan
Fax: +81-3-5228-8251
Tel: +81-3-5228-8251

c 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

In this study, we synthesized two novel carboxylic acid and carboxylate compounds, both of which had an amide group linked with an azomethine moiety to introduce photoinduced switching of the intramolecular NH⋯O hydrogen bond. We suggest that the cis-carboxylate compound forms a stronger intramolecular NH⋯O hydrogen bond than the cis-carboxylic acid compound.

Graphical abstract: Photoinduced switching of intramolecular hydrogen bond between amide NH and carboxyl oxygen

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Article information

DOI
https://doi.org/10.1039/B516049A
Article type
Paper
Submitted
11 Nov 2005
Accepted
03 Feb 2006
First published
22 Feb 2006

Org. Biomol. Chem., 2006,4, 1338-1342

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Photoinduced switching of intramolecular hydrogen bond between amide NH and carboxyl oxygen

T. Matsuhira, H. Yamamoto, A. Onoda, T. Okamura and N. Ueyama, Org. Biomol. Chem., 2006, 4, 1338 DOI: 10.1039/B516049A

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