Issue 3, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Hydrogen bonding in phthalimido carboxylic acids: cyclic voltammetric study and correlation with photochemical reactivity. Part 2.1 Aliphatic and aromatic acids†

Michael Oelgemöller,*a   Andreas Haeuseler,*b   Michael Schmittel,*b   Axel G. Griesbeck,c   Johann Lexc  and  Yoshihisa Inouea  

* Corresponding authors

a Inoue Photochirogenesis Project, ERATO, JST, 4-6-3 Kamishinden, Toyonaka-shi, Osaka, 560-0085, Japan

b FB 8 - OC1 (Chemie-Biologie) der Universität-GH Siegen, Adolf-Reichwein-Straße 2, D-57068 Siegen, Germany

c Institut für Organische Chemie, Universität zu Köln, Greinstraße 4, D-50939 Köln, Germany

Abstract

Cyclic voltammetry was applied as a useful tool for the detection and semiquantitative assessment of hydrogen bonding in phthalimidoalkyl and aryl carboxylic acids in solution. Both intra- and intermolecular hydrogen bonding could be detected and were assigned on the basis of base (DBU), acid (trifluoromethanesulfonic acid), solvent (MeCN vs. DMF), concentration and scan rate effects, as well as multisweep experiments. The observation of intramolecular hydrogen bonding neatly correlates with the reactivity pattern of the corresponding phthalimido carboxylic acids in photodecarboxylation reactions.

Graphical abstract: Hydrogen bonding in phthalimido carboxylic acids: cyclic voltammetric study and correlation with photochemical reactivity. Part 2.1 Aliphatic and aromatic acids

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Article information

DOI
https://doi.org/10.1039/B105860F
Article type
Paper
Submitted
03 Jul 2001
Accepted
09 Jan 2002
First published
04 Feb 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 676-686

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Hydrogen bonding in phthalimido carboxylic acids: cyclic voltammetric study and correlation with photochemical reactivity. Part 2. Aliphatic and aromatic acids

M. Oelgemöller, A. Haeuseler, M. Schmittel, A. G. Griesbeck, J. Lex and Y. Inoue, J. Chem. Soc., Perkin Trans. 2, 2002, 676 DOI: 10.1039/B105860F

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