Issue 20, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Syntheses and characterization of 5-substituted hydantoins and thiazolines—implications for crystal engineering of hydrogen bonded assemblies. Crystal structures † of 5-(2-pyridylmethylene)hydantoin, 5-(2-pyridylmethylene)-2-thiohydantoin, 5-(2-pyridylmethylene)thiazolidine-2,4-dione, 5-(2-pyridylmethylene)rhodanine and 5-(2-pyridylmethylene)pseudothiohydantoin ‡

Mubarik M. Chowdhry,§a   D. Michael P. Mingos,a   Andrew J. P. Whitea  and  David J. Williamsa  

a Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London, UK

Abstract

A series of six potentially bidentate ligands composed of 5-membered heterocyclic rings with methylenepyridyl substituents are described. These molecules are potentially bifunctional, acting as bidentate ligands to metal centres whilst retaining on their periphery a range of groups capable of forming triple hydrogen bonds. Their metal complexes have the potential to display interesting magnetic, optical and electrochemical properties when the hydrogen bonds are used for the crystal engineering of solid state materials. Here we report the synthesis and characterization of the six closely related molecules, 5-(2-pyridylmethylene)hydantoin I, 5-(2-pyridylmethylene)-2-thiohydantoin II, 5-(2-pyridylmethylene)thiazolidine-2,4-dione III, 5-(2-pyridylmethylene)rhodanine IV, 5-(2-pyridylmethylene)pseudothiohydantoin V and 5-(2-pyridylmethylene)-2-imino-4-amino-2,5-dihydrothiazole VI. The solid state structures of I–VI have been studied using natural abundance solid state 15N NMR spectroscopy and the single crystal structures of I–V are discussed.

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Article information

DOI
https://doi.org/10.1039/B004312P
Article type
Paper
Submitted
31 May 2000
Accepted
10 Aug 2000
First published
03 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3495-3504

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Syntheses and characterization of 5-substituted hydantoins and thiazolines—implications for crystal engineering of hydrogen bonded assemblies. Crystal structures of 5-(2-pyridylmethylene)hydantoin, 5-(2-pyridylmethylene)-2-thiohydantoin, 5-(2-pyridylmethylene)thiazolidine-2,4-dione, 5-(2-pyridylmethylene)rhodanine and 5-(2-pyridylmethylene)pseudothiohydantoin

M. M. Chowdhry, D. M. P. Mingos, A. J. P. White and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 2000, 3495 DOI: 10.1039/B004312P

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