CSIRO Publishing Home Books & CDs Journals About Us Shopping Cart
Australian Journal of Chemistry
  An international journal for chemical science
You are here: Journals > Australian Journal of Chemistry   
Search
 
 
  Advanced Search
   
Journal Home
General Information
Scope
Editorial Board
Print Publication Dates
Online Content
For Authors
How to Order

 Most Read
Visit our Most Read page regularly to keep up-to-date with the most downloaded papers in this journal.

 Early Alert
Subscribe to our email Early Alert or RSS feeds for the latest journal papers.

 

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 and 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


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.

Australian Journal of Chemistry 59(5) 320–328    doi:10.1071/CH06074
Submitted: 27 February 2006    Accepted: 15 May 2006    Published: 13 June 2006





   
Subscriber Login
Username:
Password:  

 View
Issue Contents
PDF (679 KB) $25
Export Citation
Cited by
 Tools
Print
Email this page
    


 
Top  Email this page
 


Legal & Privacy | Sitemap | Contact Us | Help

CSIRO

© CSIRO 1996-2010