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Article << Previous     |     Next >>   Contents Vol 59(5)

Molecular Recognition in Proton-Transfer Compounds of Brucine with Achiral Substituted Salicylic Acid Analogues

Graham Smith A D, Urs D. Wermuth A, Peter C. Healy B, Jonathan M. White C

A School of Physical and Chemical Sciences, Queensland University of Technology, Brisbane QLD 4001, Australia.
B School of Science, Griffith University, Nathan QLD 4111, Australia.
C School of Chemistry, University of Melbourne, Parkville VIC 3052, Australia.
D Corresponding author. Email: g.smith@qut.edu.au
 
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Abstract

The 1:1 proton-transfer brucinium compounds from the reaction of the alkaloid brucine with 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, and 5-sulfosalicylic acid, namely anhydrous brucinium 5-nitrosalicylate (1), brucinium 3,5-dinitrosalicylate monohydrate (2), and brucinium 5-sulfosalicylate trihydrate (3) have been prepared and their crystal structures determined by X-ray crystallography. All structures further demonstrate the selectivity of brucine for meta-substituted benzoic acids and comprise three-dimensional hydrogen-bonded framework polymers. Two of the compounds (1 and 3) have the previously described undulating brucine sheet host-substructures which incorporate interstitially hydrogen-bonded salicylate anion guest species and additionally in 3 the water molecules of solvation. The structure of 2 differs in having a three-centre brucinium–salicylate anion bidentate N+–H···O(carboxyl) hydrogen-bonding association linking the species through interstitial associations involving also the water molecules of solvation. A review of the crystallographic structural literature on strychnine and brucine is also given.

   
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