William H. Pirkle
Emeritus Professor of Chemistry
Professor William H. Pirkle received his B.S. from the University of California, Berkeley, in 1958 and his Ph.D. from the University of Rochester in 1963. He joined the faculty at Illinois in 1964. His research interests are in organic chemistry. Research in his group entailed the use of chromatographic and spectroscopic (especially NMR) techniques to study the details of how one enantiomer of a substance discriminates between the enantiomers of other substances.
Research
Research in our group entails the use of chromatographic and spectroscopic (especially NMR) techniques to study the details of how one enantiomer of a substance discriminates between the enantiomers of other substances. To the extent that one understands, one can control "chiral recognition." This capability has many practical applications. For example, "designed" chiral selectors, when bonded to the surface of silica gel particles, afford chiral packings for high-performance liquid chromatography columns. These columns are used to separate the enantiomers of many compounds, including a large number of pharmaceuticals. Incorporated into polymers, chiral selectors can be formed into enantioselective membranes that can be used for large-scale (potentially process-scale) resolutions. We are now working to apply chiral recognition principles, as understood from our other studies, to asymmetric synthesis.
A prerequisite for studying chiral selectors is the ability to prepare the specific selectors to be studied. Hence, members of our group are involved in organic synthesis as well as chromatographic and spectroscopic studies. In this sense, our research is on the organic/analytical boundary.
Publications
"Two-component Chiral Phase Transfer Catalysts: Enantioselective Esterification of an N-Acylated Amino Acid," S. E. Snyder and W. H. Pirkle, Organic Letters, 3, 1821-1823 (2001).
"Chiral Recognition in the Solid State, Crystallographically Characterized Disasteriomeric Co-Crystals Between A Synthetic Chiral Selector and a Representative Chiral Gues," Michael Koscho, Patrick Spence and William H. Pirkle, Chirality, (in press).
"Structural Optimization of a Chiral Selector for Use in Preparative Enantioselective Chromatography," Michael Koscho and William H. Pirkle, J. Chromatogr., 840, 151-158 (1999).
"Separation of the Enantiomers of N-Benzyloxycarbonyl, 9-Fluorenylmethoxycarbonyl and Phthaloyl Protected -Amino Acids and their Ester or Amide Derivatives," Wonjae Lee and William H. Pirkle, Bull. Korean Chem. Soc., 19, (11) 1277-1280 (1998).
Awards
- Chirality Medal - Swedish Academy of Pharmaceutical Sciences
- American Chemical Society Award in Chromatography
- Alfred P. Sloan Fellowship
- British Chromatographic Society A. S. Martin Medal
- DuPont Young Faculty Award
- Robert Boyle Gold Medal for Analytical Chemistry, Royal Society of Chemistry
- Isco Award for Instrumentation for Chemical Separation
- 1998 Award in Separation Science, Eastern Analytical Symposium
- 2000 Dal Nogare Award
