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Conversion of a weak organic acid to a super acid in the gas phase
Author(s) -
Fattahi Alireza,
Tavasoli Elham
Publication year - 2008
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1292
Subject(s) - chemistry , benzoic acid , acetic acid , endothermic process , gas phase , dissociation (chemistry) , inorganic chemistry , metal , organic acid , ionic bonding , acid dissociation constant , medicinal chemistry , ion , organic chemistry , adsorption , aqueous solution
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 298 K, 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.