Merging constitutional and motional covalent dynamics in reversible imine formation and exchange processes

Journal of the American Chemical Society
Petr Kovaříček, Jean-Marie Lehn

Abstract

The formation and exchange processes of imines of salicylaldehyde, pyridine-2-carboxaldehyde, and benzaldehyde have been studied, showing that the former has features of particular interest for dynamic covalent chemistry, displaying high efficiency and fast rates. The monoimines formed with aliphatic α,ω-diamines display an internal exchange process of self-transimination type, inducing a local motion of either "stepping-in-place" or "single-step" type by bond interchange, whose rate decreases rapidly with the distance of the terminal amino groups. Control of the speed of the process over a wide range may be achieved by substituents, solvent composition, and temperature. These monoimines also undergo intermolecular exchange, thus merging motional and constitutional covalent behavior within the same molecule. With polyamines, the monoimines formed execute internal motions that have been characterized by extensive one-dimensional, two-dimensional, and EXSY proton NMR studies. In particular, with linear polyamines, nondirectional displacement occurs by shifting of the aldehyde residue along the polyamine chain serving as molecular track. Imines thus behave as simple prototypes of systems displaying relative motions of molecular mo...Continue Reading

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Citations

Dec 28, 2012·Journal of the American Chemical Society·Koushik AcharyyaPartha Sarathi Mukherjee
May 16, 2013·Journal of the American Chemical Society·Araceli G CampañaUrszula Lewandowska
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