On the activation of PhICl2 with pyridine

Article

Poynder, Tiffany B., Orue, Analia I. Chamorro, Tania, Sharp-Bucknall, Lachlan, Flynn, M., Wilson, David J. D., Arachchige, K., Clegg, J.K. and Dutton, Jason L.. 2021. "On the activation of PhICl2 with pyridine." Chemical Communications. 57 (40), pp. 4970-4973. https://doi.org/10.1039/d1cc01567b
Article Title

On the activation of PhICl2 with pyridine

ERA Journal ID1319
Article CategoryArticle
AuthorsPoynder, Tiffany B., Orue, Analia I. Chamorro, Tania, Sharp-Bucknall, Lachlan, Flynn, M., Wilson, David J. D., Arachchige, K., Clegg, J.K. and Dutton, Jason L.
Journal TitleChemical Communications
Journal Citation57 (40), pp. 4970-4973
Number of Pages4
Year18 May 2021
PublisherThe Royal Society of Chemistry
Place of PublicationUnited Kingdom
ISSN1359-7345
1364-548X
Digital Object Identifier (DOI)https://doi.org/10.1039/d1cc01567b
Abstract

It has been previously proposed that pyridines can activate PhICl2 by displacing a chloride and forming the [PhI(Pyr)(Cl)]+ cation as a reactive intermediate. Here we show that pyridine does not displace chloride, but rather forms a weak complex with the iodine via halogen bonding along the C-I bond axis. This interaction is interrogated by NMR, structural, charge density, and theoretical investigations, which all indicate that pyridine does not activate PhICl2 as proposed.

Keywordsbenzene derivative; iodine; iodobenzene dichloride; pyridine; unclassified drug
ANZSRC Field of Research 2020340503. Organic chemical synthesis
Public Notes

File reproduced in accordance with the copyright policy of the publisher/author.

Byline AffiliationsLa Trobe University
University of Queensland
Permalink -

https://research.usq.edu.au/item/wz49x/on-the-activation-of-phicl2-with-pyridine

Log in to edit

Download files

Accepted Version
on-the-activation-of-ph-i-cl2-with-pyridine.pdf
File access level: Anyone

  • 36
    total views
  • 50
    total downloads
  • 1
    views this month
  • 1
    downloads this month

Export as

Related outputs

Circular economy barriers in Australia: How to translate theory into practice?
Feldman, Jessica, Seligmann, Hannah, King, Sarah, Flynn, Matthew, Shelley, Tristan, Helwig, Andreas and Burey, Paulomi (Polly). 2024. "Circular economy barriers in Australia: How to translate theory into practice?" Sustainable Production and Consumption. 45, pp. 582-597. https://doi.org/10.1016/j.spc.2024.02.001
Construction and Deconstruction: Materials and substances from 'waste'
Burey, Paulomi, Feldman, Jessica, Seligmann, Hannah, Song, Eric, Flynn, Matthew, Helwig, Andreas, Gharineiat, Zahra, Seneviratne, Dinuki, Whiteside, Eliza, Shelley, Tristan, Priesler, Nils, Manalo, Allan, Mirzaghorbanali, Ali, Nourizadeh, Hadi, Roberts, Michae, Nicol, Rose, Redmond, Petrea, Lynch, Mark, Dearnaley, John, ..., Germon, Geoff. 2023. "Construction and Deconstruction: Materials and substances from 'waste'." Chemistry in Australia. (June-August 2023), pp. 16-21.
Atom-economic synthesis of an oligomeric P/N-containing fire retardant towards fire-retarding and mechanically robust polylactide biocomposites
Feng, Jiabing, Lu, Yixia, Xie, Hongyan, Zhang, Yan, Huo, Siqi, Liu, Xiaohuan, Flynn, Matt, Xu, Zhiguang, Burey, Paulomi, Lynch, Mark, Wang, Hao and Song, Pingan. 2023. "Atom-economic synthesis of an oligomeric P/N-containing fire retardant towards fire-retarding and mechanically robust polylactide biocomposites." Journal of Materials Science and Technology. 160, pp. 86-95. https://doi.org/10.1016/j.jmst.2023.04.003
Glycolaldehyde as a Bio-Based C1 Building Block for Selective N-Formylation of Secondary Amines
Flynn, Matthew T., Liu, Xin, Dell'Acqua, A., Rabeah, Jabor, Brueckner, Angelika, Barath, Eszter, Tin, Sergey and de Vries, Johannes G.. 2022. "Glycolaldehyde as a Bio-Based C1 Building Block for Selective N-Formylation of Secondary Amines." ChemSusChem: chemistry and sustainability, energy and materials. 15 (20), pp. 1-6. https://doi.org/10.1002/cssc.202201264
An HIV epidemic is ready to emerge in the Philippines
Farr, Anna C. and Wilson, David. 2010. "An HIV epidemic is ready to emerge in the Philippines." Journal of the International AIDS Society. 13 (1). https://doi.org/10.1186/1758-2652-13-16