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Allison Dick, Ph.D.

Assistant Professor, Organic Chemistry

On Faculty since 2017
630.752.5406


allison.dick@wheaton.edu

Dr. Dick (Dr. Allison to many of her students) is 3rd generation Wheaton alum who is pleased to have returned as a faculty member. Her interest in teaching began as a Wheaton student when she served as a TA and lab prep assistant for organic labs. In graduate school at the University of Michigan, she continued her role as a graduate student instructor (GSI) for undergraduate organic labs, earning the title of Outstanding Graduate Student Instructor after her first year. She continued as a GSI for first year graduate courses after joining the lab of Dr. Melanie Sanford, ultimately graduating as her first PhD student. Melanie has since become highly regarded in the chemistry community and has received numerous awards and accolades. 

Following graduate school, Dr. Dick completed post-doctoral research in the lab of Huw Davies at University at Buffalo. Her research in both grad school and her post-doc was in the field of C-H activation, which is also the broad focus of her current independent research. After completing her post-doc, Dr. Dick worked for nine years at CAS (formerly Chemical Abstracts Service) in Columbus, OH. CAS is a division of the American Chemical Society and the creator of SciFinder®, a search tool used by chemists worldwide to access primary chemical literature. While at CAS, Dr. Dick was involved in numerous aspects of database building and project management. During her time in Columbus, she also taught a summer organic chemistry course for non-majors at Columbus State Community College. Since returning to Wheaton, Dr. Dick has enjoyed teaching, mentoring research students, and getting to know her new colleagues.

University at Buffalo
Post-doctoral researcher
2007-2008

University of Michigan
Ph.D., Chemistry
2007

Wheaton College
B.S., Chemistry
2002

American Chemical Society, Midwest Association of Chemistry Teachers at Liberal Arts College (MACTLAC)

  • Organic Chemistry I and II
  • Everyday Chemistry
  • Synthesis and Analysis
  • Organic Chemistry Research
  • Organic Chemistry
  • Organometallic Chemistry
  • Chemical Information

Detailed Study of C−O and C−C Bond-Forming Reductive Elimination from Stable C2N2O2−Ligated Palladium(IV) Complexes, Journal of the American Chemical Society
Joy M. Racowski, Allison R. Dick, and Melanie S. Sanford. 2009.
This paper describes the synthesis of a series of PdIV complexes of general structure (N∼C)2PdIV(O2CR)2 (N∼C = a rigid cyclometalated ligand; O2CR = carboxylate) by reaction of (N∼C)2PdII with PhI(O2CR)2. The majority of these complexes undergo clean C−O bond-forming reductive elimination, and the mechanism of this process has been investigated. A variety of experiments, including Hammett plots, Eyring analysis, crossover studies, and investigations of the influence of solvent and additives, suggest that C−O bond-forming reductive elimination proceeds via initial carboxylate dissociation followed by C−O coupling from a 5-coordinate cationic PdIV intermediate. The mechanism of competing C−C bond-forming reductive elimination from these complexes has also been investigated and is proposed to involve direct reductive elimination from the octahedral PdIV centers.

Carbon−Nitrogen Bond-Forming Reactions of Palladacycles with Hypervalent Iodine Reagents, Organometallics
Allison R. Dick, Matthew S. Remy, Jeff W. Kampf, and Melanie S. Sanford. 2007.
Palladium(II) complexes containing bidentate cyclometalated C∼N chelating ligands are shown to react with PhINTs at room temperature to insert “NTs” into the Pd−C bond. This “NTs” insertion reaction has been applied to palladacyclic complexes of azobenzene, benzo[h]quinoline, and 8-ethylquinoline. The newly aminated organic ligands can be liberated from the metal center by protonolysis with trifluoroacetic acid or HCl.

A Simple Catalytic Method for the Regioselective Halogenation of Arenes, Organic Letters
Dipannita Kalyani, Allison R. Dick, Waseem Q. Anani and Melanie S. Sanford. 2006.
This paper describes a mild palladium-catalyzed method for the regioselective chlorination, bromination, and iodination of arene C−H bonds using N-halosuccinimides as oxidants. These transformations have been applied to a wide array of substrates and can provide products that are complementary to those obtained via conventional electrophilic aromatic substitution reactions.

Unusually Stable Palladium(IV) Complexes:  Detailed Mechanistic Investigation of C−O Bond-Forming Reductive Elimination, Journal of the American Chemical Society
Allison R. Dick, Jeff W. Kampf, and Melanie S. Sanford. 2005.
This communication describes the synthesis of a family of unusually stable palladium(IV) complexes containing two chelating 2-phenylpyridine ligands and two benzoates. These complexes undergo clean C−O bond-forming reductive elimination upon heating, and the mechanism of this catalytically relevant process has been studied in detail. Solvent effects, crossover experiments, Eyring plots (which show ΔS⧧ of −1.4 ± 1.9 and 4.2 ± 1.4 in CDCl3 and DMSO, respectively), and Hammett analysis (which shows ρ = −1.36 ± 0.04 upon substitution of the para-benzoate substituent) all suggest that reductive elimination does not proceed via initial dissociation of a benzoate ligand. Instead, an unusual mechanism involving pre-equilibrium dissociation of the N-arm of the phenylpyridine ligand is proposed.

Platinum Model Studies for Palladium-Catalyzed Oxidative Functionalization of C−H Bonds, Organometallics
Allison R. Dick, Jeff W. Kampf and Melanie S. Sanford. 2005.
The synthesis of (CN)PtII(acac) complexes (CN = benzo[h]quinoline, 8-methylquinoline) and their oxidation with PhI(OAc)2 are reported as a model system for palladium-catalyzed C−H bond functionalization. Dimeric PtIII−PtIII complexes containing a bridging acetate ligand are obtained in HOAc, and monomeric PtIV complexes incorporating alkoxide and acetate ligands are obtained in MeOH, EtOH, and iPrOH. The implications of these results for the mechanism of analogous Pd-catalyzed reactions is discussed.

The field of C-H activation, or C-H functionalization, includes a wide variety of selective transformations of carbon-hydrogen bonds. These bonds are ubiquitous in organic molecules, but historically suffered from low or unselective reactivity. The use of transition metal catalysts has allowed many new reactions to be developed, many of which occur under relatively mild reaction conditions. Dr. Dick is applying her background in this field to attempt the synthesis of cyclic phosphonamides, which contain a high oxidation state phosphorus atom bonded to a nitrogen atom, via intramolecular formation of a carbon-nitrogen bond in place of a normally unreactive carbon-hydrogen bond. These cyclic phosphonamides are similar in structure to sulfur analogs called sultams, many of which possess desirable medicinal properties, such as meloxicam. Due to the difficulty in their synthesis, however, many fewer cyclic phosphonamides have been isolated, so their properties are not as well studied. A mild and selective route to their synthesis could open new doors to study both their chemical and medicinal properties.