ChloroquineV1, Main, Exploration, bibRecord, 001C07

Solvent-induced-effects: self-association of positively charged pi systems

Identifieur interne : 001C07 ( Main/Exploration ); précédent : 001C06; suivant : 001C08

Solvent-induced-effects: self-association of positively charged pi systems

Auteurs : Eric Buisine [France] ; Katherine De Villiers [Afrique du Sud] ; Timothy Egan [Afrique du Sud] ; Christophe Biot [France]

Source :

Journal of the American Chemical Society [ 0002-7863 ] ; 2006.

RBID : Hal:hal-00098658

Abstract

Antimalarial cationic drugs, such as chloroquine (CQ) and ferroquine (FQ), form stable dimer structures not only in the solid state but also in solution. The short distances (3.3-3.5 Å) observed between the positively charged quinolinium rings suggest that this self-association process is driven by pi/pi stacking interactions. Nevertheless, the strength of these dispersive forces is likely not sufficient to overcome the strong repulsive +/+ electrostatic effects. The question of the exact role of the environment, particularly the solvent, is clearly raised here. Characterization of these unconventional stabilizing nonbonding interactions which we have named +-pi/+-pi is therefore of great importance. In the present work, we describe theoretical calculations and NMR experiments undertaken to probe the nature and the strength of +-pi/+-pi interactions occurring upon self-association of FQ and CQ molecules in water.

Url:

https://hal.archives-ouvertes.fr/hal-00098658

DOI: 10.1021/ja061755u

Affiliations:

Afrique du Sud, France

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Le document en format XML

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<front><div type="abstract" xml:lang="en">              <p>Antimalarial cationic drugs, such as chloroquine (CQ) and ferroquine (FQ), form stable dimer structures not only in the solid state but also in solution. The short distances (3.3-3.5 Å) observed between the positively charged quinolinium rings suggest that this self-association process is driven by pi/pi stacking interactions. Nevertheless, the strength of these dispersive forces is likely not sufficient to overcome the strong repulsive +/+ electrostatic effects. The question of the exact role of the environment, particularly the solvent, is clearly raised here. Characterization of these unconventional stabilizing nonbonding interactions which we have named +-pi/+-pi is therefore of great importance. In the present work, we describe theoretical calculations and NMR experiments undertaken to probe the nature and the strength of +-pi/+-pi interactions occurring upon self-association of FQ and CQ molecules in water.</p>
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Solvent-induced-effects: self-association of positively charged pi systems

Solvent-induced-effects: self-association of positively charged pi systems

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