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

Graham Smith; Urs D. Wermuth; Peter C. Healy; Jonathan M. White

doi:10.1071/CH06074

RESEARCH 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 and Jonathan M. White ^C

+ Author Affiliations

- Author Affiliations

^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

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

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.

Acknowledgements

The authors acknowledge financial support from the School of Physical and Chemical Sciences, Queensland University of Technology, the School of Science, Griffith University, and the University of Melbourne.

References

^* R1 = (Σ |F_o| – |F_c|)/Σ|F_o|). wR2 = Σ[w(F_o² – F_c²)²]/Σ[w(F_o²)²]^1/2. S = Σ[w(F_o² – F_c²)²]/(n – p)^1/2.

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

Abstract

Acknowledgements

Subscriber Login