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Assessing the persistence of the N H?N hydrogen bonding leading to supramolecular chains in molecules related to the anti-malarial drug, chloroquine

Authors: Kaiser, C.R.; Pais, K.C.; De Souza, M.V.N.; Wardell, J.L.; Wardell, S.M.S.V.; Tiekink, E.R.T.


Abstract

Crystal packing patterns for a range of chloroquine derivatives have been investigated. For species where the amine-bound R substituent carries atoms not capable of forming significant hydrogen bonding interactions, i.e. R = methyl (1), n-propyl (2), n-butyl (3), 2-chloroethyl (4), 2-azidoethyl (5), N–H⋯N hydrogen bonding between the amine and pyridine groups predominate leading to supramolecular chains. In species carrying hydroxyl groups, i.e. R = 2-hydroxylethyl (6), 1-butanol (7), and (S)-1-butanol (8), the N–H⋯N interactions are subverted by O–H⋯N and N–H⋯O hydrogen bonding that results in the formation of 2-D arrays, establishing an hierarchy of hydrogen bonding interactions in these systems. Despite the differences in hydrogen bonding, globally, the crystal packing in all structures is similar in that the N–H⋯N mediated supramolecular chains of (1–5) aggregate into layers usually via C–H⋯π, C–Cl⋯π and π⋯π interactions. These layers, as with those formed in (6–8), stack into a 3-D arrangement being consolidated via C–H⋯Cl and π⋯π or C–Cl⋯π interactions.
Keywords: None Document Type: Research Article DOI: http://dx.doi.org/10.1039/B823058G Publication date: 27 de Fevereiro de 2009

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