Chemistry Faculty/Staff Directory
Dr. Kraig A. Wheeler
Professor - Organic Chemistry
Office: 4460 - Physical Science Bldg
Kraig Wheeler came to Eastern Illinois University in August 2005 from Delaware State University where he was a faculty member in the Department of Chemistry for twelve years. His research interests include the study of supramolecular assemblies, molecular recognition processes, predicting the organization of electrostatic contacts in competitive crystal environments, and X-ray crystallography. The majority of his recent work has focused on Asymmetric Reactions in Molecular Crystals and Quasiracemic Materials and their use as synthons for understanding the role of molecular topology in the construction of crystalline materials. He attended the University of Minnesota (1983-1987) as an undergraduate student where he was first encouraged and inspired to conduct research in solid-state organic chemistry by the late Margaret C. Etter. He received his Ph.D. from Brandeis University in 1992 with Bruce M. Foxman investigating solid phase reactivity of metal carboxylates. Prior to joining the DSU faculty, he carried out postdoctoral work with Raymond E. Davis and James K. Whitesell (1992-1993) at the University of Texas Austin.
One of his passions includes helping students experience the joys of organic chemistry – both in teaching and research. Seeing students have “light bulb” experiences and taking part in weighty classroom discussions keeps him motivated to stay a few steps ahead of his students. He teaches a collection of organic chemistry courses at EIU.
Frequently Taught CoursesAdvanced Laboratory (CHM 4915)
Modern Organic Chemistry (CHM 5420)
Sophomore Organic Chemistry Lecture and Laboratory (CHM 2440, 2445, 2840, and 2845)
Survey of Organic Chemistry (CHM 2430 and 2435)
EducationPh.D., 1992, Brandeis University, Organic Chemistry, Waltham, Massachusetts
B.A., 1987, Chemistry University of Minnesota, Minneapolis, MN
Professional OrganizationsAmerican Chemical Society
American Crystallographic Association
Council on Undergraduate Research
For more information, please visit the Speakers Bureau Webpage.
Design Strategies and Advances in Nanotechnology Asymmetric Reaction in Molecular Crystals The Conundrum of Crystals and other Science Anomalies
ResearchDr. Wheeler's research programs are directed at the study of molecular crystals and engineered functional materials. Design of novel cocrystalline quasiracemic compounds, noncentrosymmetric molecular assemblages and crystal engineering via molecular topology. Chemical reactions in molecular crystals. Construction of predictable molecular frameworks by exploiting strong and weak intermolecular interactions. Nanoporous materials derived from coordination polymer and robust donor-acceptor molecular architectures. Single-crystal X-ray crystallography.
Publications(Last Five Years)
“Electrophilic Cyclizations of 2-Fluoroalk-3-yn-1-ones: Room-Temperature Synthesis of Diverse 2,5-Disubstituted 3,4-Fluorohalofurans,” Eur. J. Org. Chem. 2011, 2767-2771. Li, Y.; Wheeler, K. A.; Dembinski, R.
“Enantiocontrolled Solid-State Photodimerizations via a Chiral Sulfonamidecinnamic Acid,” Crystal Engineering Communications 2011, 13, 3134-3137, Wheeler, K.A.; Wiseman, J.D.; Grove, R.C. (selected as Hot article, cover)
“Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Six-Membered Cyclic Ketones: An Enamine/Metal Lewis Acid Bifunctional Approach,” Angewandte Chemie, International Edition 2011, 50, 3484-3488. Xu, Z.; Liu, L.; Wheeler, K.; Wang, H.
“Network Dimensionality and Ligand Flexibility in Lanthanide Terephthalate Hydrates,”Journal of Molecular Structure 2011, 985, 109-119. Zehnder, R. A.; Renn, R. A.; Pippin, E.; Zeller, M.; Wheeler, K.A.; Carr, J.A.; Fontaine, N.; McMullen, N.C.
“Intramolecular Exchange of Coordinated and Dangling Phosphines in Pentacarbonyl Group 6 Complexes of 1,1,2-Tris(diphenylphosphino)ethane,” Inorganica Chimica Acta 2010, 364, 176-184. Keiter, R.L.; Ye, P.; Keiter, E.A.; Benson, J.W.; Lin, W.; Brandt, D.E.; Southern, J.S.; Rheingold, A.L.; Guzei, I.; Wheeler, K.A.; Cary, L.W.
“Mechanistic Studies of the Phosphine-Catalyzed Homodimerization of Ketoketenes,”Wei, P.-H.; Ibrahim, A. A.; Mondal, M.; Nalla, D.; Harzmann, G. D.; Tedeschi, F. A.; Wheeler, K. A.; Kerrigan, N. J. Tetrahedron Letters 2010, 51, 6690-6694.
“Gold(I)-Catalyzed Cycloisomerization of 2-Fluoroalk-3-yn-1-ones: Synthesis of 2,5-Substituted 3-Fluorofurans,” Advanced Synthesis & Catalysis 2010, 352, 2761-2766. Li, Y.; Wheeler, K.A.; Dembinski, R.
“A Photoreactive Crystalline Quasiracemate,” Chemical Communications 2010, 46, 7322-7324. Grove, R.C.; Malehorn, S.H.; Breen, M.E.; Wheeler, K.A.
“10,12-Dimethylpteridino[6,7-f][1,10]phenanthroline-11,13(10H,12H)-dione-chloroform (1/1),” Acta Crystallographica 2010, E66, 2288. Olaprath, W.; Roden, J.; Wheeler, K.A.; McGuire, M.E.
“Structural and Spectroscopic Characterization of Mer-[RhBr3(Me2pzH)3] (Me2pzH = 3, 5-Dimethylpyrazole); Interpreting the Results with Density Functional Theory Calculations,”Journal of Chemical Crystallography 2010, 40, 583-590. Abrahams, M.M.; Cushing, G.W.; Pickett, Z.N.; Howard, W.A.; Wheeler, K.A.
“Synthesis, Crystal Structure, and Spectroscopy of cis-Dichlorotetrakis(2,6-Dimethylphenyl Isocyanide)Iron(II),” Journal of Chemical Crystallography 2010,40, 482-485. Perry, M.C.; Law, T.C.; Wheeler, K.A.
“Phosphine-Catalyzed Asymmetric Synthesis of b-Lactones from Arylketoketenes and Aromatic Aldehydes,”Organic Letters, 2010, 12, 1664-1667. Mondal, M.; Ibrahim, A.A.; Wheeler, K.A.; Kerrigan, N.J.
“A Three-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones,”Chemistry--A European Journal 2010, 16, 2972-2976. Xu, Z.; Buechler, T.; Wheeler, K.; Wang, H.
“Functionalized O-Alkyldithiocarbonates: A New Class of Ligands Designed for Luminescent Heterometallic Materials,”Inorganic Chemistry 2010, 49, 2624-2629. Semeniuc, R.F.; Reamer, T.J.; Blitz, J.P.; Wheeler, K.A.; Smith, M.D.
“Synthesis of bipyridine-N-oxides and bipyridine-N,N'-dioxides,” Heterocyclic Communications 2009, 15, 181-188. McKay, S. E.; Lashlee, R. W., III; Maina, L. W.; Wheeler, K. A.; Brown, A. B.
“A Concise Approach to the Synthesis of opp-Dibenzoporphyrins through the Heck Reaction,”Organic Letters2009, 11, 4251-4253. Deshpande, R.; Jiang, L.; Schmidt, G.; Rakovan, J.; Wang, X.; Wheeler, K.; Wang, H.
“Synthesis and Structures of Two Functionalized Isobenzofurans: (3aR,7aR,4S,5S)-1,3,3a,4,5,7a-Hexahydro-5-methyl-3-oxoisobenzofuran-4-carboxylic acid and (3aα,4β,7β,7aα)-4-[(Acetyloxy)methyl]-3a,4,7,7a-tetrahydro-7-methyl-1,3-isobenzofurandione,” Journal of Chemical Crystallography 2009, 40, 76-79. Bennett, G.D.; Bringman, L.R.; Wildman, E.M.; Wheeler, K.A.
“Microwave-Assisted Zinc Chloride-Catalyzed Synthesis of Substituted Pyrroles from Homopropargylic Azides,”Tetrahedron 2009, 65, 1268-1275. Wyrebek, P.; Sniady, A.; Bewick, N.; Li, Y.; Mikus, A.; Wheeler, K.A.; Dembinski, R.
“(±)-3-Carboxy-2-(imidazol-3-ium-1-yl)propanoate,” Acta Crystallographica 2009, E65, 01424. Reeb, S.A.; Shields, M.C.; Wheeler, K.A..
“Structural Studies of Racemates and Quasiracemates. 2-(3-Bromophenoxy)propionic Acid and 2-(3-Methoxyphenoxy)propionic Acid” Crystal Growth & Design 2008, 8, 3863-3870. Breen, M.E.; Tameze, S.L.; Dougherty, W.G.; Kassel, W.S.; Wheeler, K.A. [selected as cover article]
“Room-Temperature Electrophilic 5-endo-dig Chlorocyclization of Alk-3-yn-1-ones with the Use of Pool Sanitizer: Synthesis of 3-Chlorofurans and 5-Chlorofuropyrimidine Nucleosides,” European Journal of Organic Chemistry 2008, 20, 3449-3452. Sniady, A.; Morreale, M.S.; Wheeler, K.A.; Dembinski, R. [selected as cover article]
“Structural Studies of Racemates and Quasiracemates. Chloro, Bromo, and Methyl Adducts of 2-Phenoxypropionic Acid” CrystalGrowth & Design 2008, 8, 612-619. Lineberry, A.M.; Benjamin, E.T.; Davis, R.E.; Kassel, W.S.; Wheeler, K.A.
“Rediscovering Pasteur’s Quasiracemates” Angewandte Chemie, International Edition 2008, 47, 78-81. Wheeler, K.A.; Grove, R.C.; Davis, R.E.; Kassel, W.S. [selected as the frontispiece of issue]
“2-Aminopyrimidine 3,3,3-triphenylpropanoic acid” Acta Crystallographica 2007, C63, o620-o621. Serafin, M.F.; Wheeler, K.A.
“Room Temperature Zinc Chloride-Catalyzed Cycloisomerization of Alk-3-yne-1-ones: Synthesis of substituted furans,” Organic Letters 2007, 9, 1175-1178. Snaidy, A.; Durham, A.; Morreale, Marco, S.; Wheeler, K. A.; Dembinski, R.
Conference Presentations(Selected Presentations - Last Five Years)
“Sulfonamidecinnamic Acids: Merging Supramolecular Asymmetry and Programmed Crystal Reactivity,” the American Crystallographic Association National Meeting, New Orleans, LA, May 29-June 2, 2011.
“Asymmetric Reactions in Molecular Crystals,”invited talk, 241st American Chemical Society National Meeting, Anaheim, CA, March 27-31, 2011.
"Submitting a Successful MRI Proposal,” Council on Undergraduate Research 13th National Conference, Weber State University, Ogden, UT, June 20, 2010. [co-presented with Samuel Abrash (Univ. Richmond) and Myriam Cotten (Hamilton College)].
“Managing Asymmetric Reactions via Molecular Crystals,” Gordon Research Conference on Crystal Engineering, Waterville Valley Resort, Waterville Valley, NH, May 6-10, 2010.
“Managing Asymmetric Reactions via Molecular Crytals,” invited talk, Knox College, Galesburg, IL, February 11, 2010.
"Conceptualizing Reaction Mechanisms Using Crystallographic Data,” 238th American Chemical Society National Meeting, Washington, DC, August 16-20, 2009.
“Controlling Molecular Assemblies via Quasiracemates,” invited talk, Indiana State University, Terra Haute, IN, March 31st, 2009.
“Exploring the Details of Reaction Mechanisms Using Crystallographic Data,” 20th Biennial Conference on Chemical Education, Indiana University, Bloomington, IN, July 27-31, 2008.
“Managing Supramolecular Assemblies using Molecular Shape,” invited talk at the American Crystallographic Association National Meeting, Knoxville, TN, May 31-June 5, 2008.
“Shaping Supramolecular Assemblies via Molecular Shape,” invited talk, Oakland University, Rochester, MI, March 19, 2008.
“Considerations of Molecular Topology for the Design of Supramolecular Assemblies,” invited talk, Crystallography Summer School, University of California at San Diego, LaJolla, CA. July 29th - August 8th, 2007.
“Diffraction Basics: Getting Started,” invited talk, Crystallography Summer School, University of California at San Diego, LaJolla, CA. July 29th - August 8th, 2007.
“Training Molecules To Get Along Via Shape-Based Molecular Recognition,” invited talk, Bradley University, Peoria, IL. September 27th, 2007.
Funding & GrantsFunding Agencies - Last Five Years
National Science Foundation (RUI and MRI)
American Chemical Society Petroleum Research Foundation