On the Bonding in Bis-pyridine Iodonium Cations*
Dayne C. Georgiou A , Phillip Butler A , Elisse C. Browne A , David J. D. Wilson A B and Jason L. Dutton A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Vic. 3086, Australia.
B Corresponding authors. Email: david.wilson@latrobe.edu.au; j.dutton@latrobe.edu.au
Australian Journal of Chemistry 66(10) 1179-1188 https://doi.org/10.1071/CH13202
Submitted: 24 April 2013 Accepted: 20 May 2013 Published: 14 June 2013
Abstract
A study on the bonding in bis-pyridine halonium cations has been carried out using both theoretical and synthetic techniques. The primary thrust for the study is to highlight the opportunities potentially afforded by considering iodine as a Lewis acid in a classic coordination sense. Our results suggest that the iodine dipyridine complex ([pyr-I-pyr]+) can be considered as a coordination complex of [I]+. The lighter bromine and chlorine analogues are more towards the covalent rather than the dative side of bonding, while [pyr-F-pyr]+ is best described as an ion-molecule complex with one strong covalent F-pyr bond and one weak F-pyr dispersion interaction. Finally, theoretical and synthetic studies suggest that the commercially available [pyr-F]+ cation cannot be considered as a coordination complex of ‘F+’, despite its use as a source of electrophilic fluorine.
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