Richard A. Kjonaas

Professor
Organic Chemistry

B.S., 1967-1971, Valley City State College
Ph.D., 1973-1978, Purdue University

Postdoctoral Experience
1978-1979, The Ohio State University

Office: S-051F
Phone: (812) 237-2237
E-mail: richard.kjonaas@indstate.edu

Teaching Awards

Blue Key Outstanding Faculty Award
Caleb Mills Distinguished Teaching Award
College of Arts and Sciences Educational Excellence Award

Research Summary

Much of the research of Dr. Kjonaas and his research group has traditionally involved the development of new reagents and methods for the synthesis of organic molecules. In the past, this work has included the use of dilithio acetoacetate and dimethyl organozincates (see equation below) as reagents for making carbon-carbon bonds. Some more current work is focused on the use of trifluoroacetic anhydride as a reagent for the dehydration of aldoximes to give nitriles as well as the use of sodium percarbonate as an oxidizing agent.

The group has also become interested in the synthesis of various derivatives of phytanol for use as vaccine adjuvants. This work is in collaboration with Professor S.K. Ghosh and his research group in the Life Sciences Department. Examples of these phyanol derivatives include phytanyl α-D-mannopyranoside as well as its β anomer (see below).

Recent Presentations

1. R. A. Kjonaas, L. R. Edenburn, P. E. Williams, "Analgesic synthesis in undergraduate laboratory courses: Aspirin-70 years, phenacetin-35 years, and now ibuprofen" 238th ACS National Meeting, Washington, DC, August 16-20, 2009.

2. P. E. Williams, D. A. Counce, R. A. Kjonaas, "Studies in the preparation of Grignard reagents from ortho, meta, and para substituted secondary benzylic chlorides and bromides" 237th ACS National Meeting, Salt Lake City, UT, March 22-26, 2009.

3. M. L. Schulte and R. A. Kjonaas, "Preparation and characterization of alpha phytanyl D-mannopyranoside" 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008.

4. L. R. Edenburn and R. A. Kjonaas, "Studies in the development of an ibuprofen preparation suitable for use in introductory organic chemistry laboratory courses" 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008.

Selected Publications

D. M. Zhilin and R. A. Kjonaas, "A Simple Apparatus for Vacuum Filtration" Journal of Chemical Education, 2013, 90: 142-143.

R. A. Kjonaas, "Counting Heteroatoms, Rings, and pi-Bonds as a Way of Recognizing and Quantifying Organic Oxidation and Reduction" Journal of Chemical Education, 2011, 88: 1601-1602.

R. A. Kjonaas, P. E. Williams, D. A. Counce, and L. R. Crawley, "Synthesis of Ibuprofen in the Introductory Organic Laboratory" Journal of Chemical Education, 2011, 88: 825-828.

1. R. A. Kjonaas and A. E. Clemons, "The Baeyer-Villiger Oxidation with Trifluoroacetic Acid and Household Sodium Percarbonate" Journal of Chemical Education, 2008, 85: 827-828.

2. R. A. Kjonaas and R. J. F. Tucker, "A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides: Permanent Magnet Carbon-13 NMR in the First-Semester Organic Chemistry Lab" Journal of Chemical Education, 2008, 85:100-101.

3. S.-Y. Lim, M. Meyer, R. A. Kjonaas, and S. K. Ghosh, "Phytol-based novel adjuvants in vaccine formulation: 1. Assessment of safety and efficacy during stimulation of hormonal and cell-mediated immune responses" Journal of Immune Based Therapies and Vaccines, 2006, 4:6.

4. S.-Y. Lim, A. Bauermeister, R. A. Kjonaas, and S. K. Ghosh, "Phytol-based novel adjuvants in vaccine formulation: 2. Assessment of efficacy in the induction of protective immune responses to lethal bacterial infections to mice" Journal of Immune Based Therapies and Vaccines, 2006, 4:5.

5. R. A. Kjonaas and S.P. Mattingly, "Acid Catalyzed Isomerization of Carvone to Carvacrol" Journal of Chemical Education, 2005, 82:1813-1814.

6. J. Zhang, R. A. Kjonaas, and W. H. Flurkey, "Does N-Hydroxyglycine Inhibit Plant and Fungal Laccases?" Phytochemistry, 1999, 52:775-783.

7. R. A. Kjonaas , J. L. Soller, and L. A. McCoy, "Identification of Volatile Flavor Components by Headspace Analysis, " Journal of Chemical Education, 1997, 74:1104-1105.

8. R. A. Kjonaas, "Amyl: A Misunderstood Word," Journal of Chemical Education, 1996, 73:1127-1129.

9. R. A. Kjonaas, "A Source of Isomer Drawing Assignments," Journal of Chemical Education, 1992, 69:452-456.

10. R. A. Kjonaas and B. A. Riedford, "A Study of the Lucas Test," Journal of Chemical Education, 1991, 68:704-706.

11. R. A. Kjonaas and R. K. Hoffer, "Regiospecific 1, 4-Addition with Grignard-Derived Mixed Triorganozincate Reagents," Journal of Organic Chemistry, 1988, 53:4133-4135.

12. R. A. Kjonaas, "Ketovinylation of Arylthallium Compounds Catalyzed by Lithium Tetrachloropalladate," Journal of Organic Chemistry, 1986, 51:3708-3710.

13. R. A. Kjonaas, "Number of Oxidations Relative to Methylene--A Convenient Method of Recognizing and Quantifying Organic Oxidation-Reduction," Journal of Chemical Education, 1986, 63:311-314.

14. R. A. Watson and R. A. Kjonaas, "Conjugate Addition of alpha, beta Unsaturated Ketones with Mixed Lithium Triorganozincates," Tetrahedron Letters, 1986, 27:311-314.

15. R. A. Kjonaas and E. J. Vawter, "Regioselective 1,4-Addition to alpha, beta Unsaturated Ketones with Grignard Reagents Mediated by N,N,N'- Tetramethylethylenediaminezinc(II) Chloride," Journal of Organic Chemistry, 1986, 51:3993-3996.