Issue 11, 2003
From the journal:

CrystEngComm

Facile solid-state molecular assembly: the crystal structure of the unique 2∶2 proton-transfer oxine-salicylic acid compound

Graham Smith,*a   Urs D. Wermutha  and  Jonathan M. Whiteb  

* Corresponding authors

a Centre for Instrumental and Developmental Chemistry, School of Physical and Chemical Sciences, Queensland University of Technology, G.P.O. Box 2434, Brisbane, Australia
E-mail: g.smith@qut.edu.au

b School of Chemistry, University of Melbourne, Parkville, Australia

Abstract

The previously reported product from the solid-state reaction of quinolin-8-ol (oxine) with salicylic acid has been characterized using single crystal X-ray diffraction methods and confirmed as the discrete dimeric proton-transfer sandwich compound [(C9H8NO+)2(C7H5O3–)2] (1). As with similar compounds of carboxylic acids and oxine, protonation of the quinoline nitrogen occurs. However, in the case of 1, the two salicylate anions provide unusual duplex carboxylato-(O,O′) hydrogen-bonding bridges [(oxine)-N+H⋯O,O′(salicylate)⋯H′–O′-(oxine)′] which stitch together the pairs of π–π-associated oxine cations. This structure determination may provide a possible explanation of the mechanism involved in the facile solid-state reaction of oxine with salicylic acid.

Graphical abstract: Facile solid-state molecular assembly: the crystal structure of the unique 2∶2 proton-transfer oxine-salicylic acid compound

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Article information

DOI
https://doi.org/10.1039/B210197C
Article type
Paper
Submitted
16 Oct 2002
Accepted
18 Dec 2002
First published
22 Jan 2003

CrystEngComm, 2003,5, 58-61

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Facile solid-state molecular assembly: the crystal structure of the unique 2∶2 proton-transfer oxine-salicylic acid compound

G. Smith, U. D. Wermuth and J. M. White, CrystEngComm, 2003, 5, 58 DOI: 10.1039/B210197C

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