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Conversion of a weak organic acid to a super acid in the gas phase

Fattahi, A ; Sharif University of Technology | 2008

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  1. Type of Document: Article
  2. DOI: 10.1002/poc.1292
  3. Publisher: 2008
  4. Abstract:
  5. The effects of selected metal ions on the gas-phase acidity of weak organic acids have been explored using the DFT and Moller-Plesset Perturbation Theory (MP2) calculations. The three organic acids selected for this study were acetic acid (aliphatic), benzoic acid (aromatic), and glycine (amino acid). The acidities of these compounds are compared with the acidity of their Li +-, Na+-, and K+ -complexed species. The results indicate that upon complexation with Li+, Na+, and K+ at 298K, the gas-phase acidity of acetic acid, for example, varies from 345.3 to 218.8, 230.2, and 240.1 kcal/mol, respectively (i.e., its dissociation becomes much less endothermic). These values indicate that a weak organic acid can be converted to a super acid when it is complexed with an ionic metal. Copyright © 2007 John Wiley & Sons, Ltd
  6. Keywords:
  7. Complexation ; Density functional theory ; Dissociation ; Perturbation techniques ; Reaction kinetics ; Benzoic acid ; Super acids ; Organic acids
  8. Source: Journal of Physical Organic Chemistry ; Volume 21, Issue 2 , 2008 , Pages 112-118 ; 08943230 (ISSN)
  9. URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.1292