Isolation and Structure of a Hydrogen-bonded 2,2′:6′,2″-Terpyridin-4′-one Acetic Acid Adduct
Pas Florio A , Campbell J. Coghlan A , Chih-Pei Lin A , Kei Saito A , Eva M. Campi A , W. Roy Jackson A and Milton T. W. Hearn A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.
B Corresponding author. Email: milton.hearn@monash.edu
Australian Journal of Chemistry 67(4) 651-656 https://doi.org/10.1071/CH13571
Submitted: 21 October 2013 Accepted: 27 November 2013 Published: 6 January 2014
Abstract
Herein, we report the crystal structure of a key intermediate in the synthesis of 4′-substituted-terpyridines. Our findings confirm that the terpyridin-4′-one intermediate as generated from the condensation reaction of the corresponding triketone precursor with ammonium acetate is isolated as a hydrogen-bonded adduct with acetic acid, and not, as previously reported, as the acetate salt of a protonated pyridine nitrogen. This finding provides a rationale for the behaviour and structure of substituted terpyridin-4′-ones and pyridones in both the solid state and in solution.
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