Counteranions play a large role in synthesis and catalysis but determining the best anion to use for a reaction can be difficult. Anions can have varying coordination strength to the cation depending on their sterics and electronics. A series of imidazolyl phenyl (IMP) anions have been synthesized that are similar in charge distribution and volume, but have different functionality depending on the R group on the para position of the phenyl ring, offering a range of different coordination strengths. Along with the anions, the conjugate oxonium acids can be synthesized in the form of [H(Et2O)2] [IMP-R]. [H(Et2O)2] [IMP-R] reacted with tri-n-octylamine forms tri-n-octylammonium salts. The N-H IR stretching frequency is a convenient measure of the coordination strength of IMP-R anions and also allows comparison with more conventional anions such as BF4 and BArF4. IMP oxonium acids can also be used to introduce the IMP-R anions to form salts of type [MLn] [IMP-R] via protonolysis.

Synthesis and application of substituted imidazolyl phenyl oxonium acids

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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