Issue 6, 2008

The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogenstorage

Abstract

Substituted piperidines and octahydroindoles are compared in terms of their usability as reversible organic hydrogen storage liquids for hydrogen-powered fuel cells. Theoretical Gaussian calculations indicate which structural features are likely to lower the enthalpy of dehydrogenation. Experimental results show that attaching electron donating or conjugated substituents to the piperidine ring greatly increases the rate of catalytic dehydrogenation, with the greatest rates being observed with 4-aminopiperidine and piperidine-4-carboxamide. Undesired side reactions were observed with some compounds such as alkyl transfer reactions during the dehydrogenation of 4-dimethylaminopiperidine, C–O and C–N cleavage reactions during hydrogenation and/or subsequent dehydrogenation of 4-alkoxy and 4-amino indoles, and disproportionation during the hydrogenation of 4-aminopyridine.

Graphical abstract: The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage

Article information

Article type
Paper
Submitted
27 Nov 2007
Accepted
11 Jan 2008
First published
30 Jan 2008

New J. Chem., 2008,32, 1027-1037

The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage

Y. Cui, S. Kwok, A. Bucholtz, B. Davis, R. A. Whitney and P. G. Jessop, New J. Chem., 2008, 32, 1027 DOI: 10.1039/B718209K

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