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Richard Nagorski

Professor, Organic Chemistry Associate Chair of Graduate Programs
Chemistry
Office
Science Laboratory Building - SLB 205
Office Hours
Tues. 11am-12pm, Wed. 2-3pm, or by appointment
  • About
  • Education
  • Awards & Honors
  • Research

Current Courses

299.016Independent Honor Study In Chemistry

499.016Independent Research For The Master's Thesis

422.001Mechanisms In Organic Chemistry

233.001Organic Chemistry Laboratory II

290.016Research in Chemistry

490.016Research In Chemistry

Research Interests & Areas

Areas of Current Research Interest The area of general interest within our group is the mechanisms and rate constants of reaction of biologically important molecules in water. In general, we prefer to observe the reaction of simple molecular analogs of the biological molecules of interest and extend our observations to the more complex biological molecules as our understanding of the system increases. There are two areas of current interest within the group. The first is the investigation of the stability constants and specifically, the mechanism of breakdown of carbinolamides. The general structure of carbinolamides is as shown in Scheme 1, and allows for great diversity of groups given the three possible positions of substitution. We are interested in these compounds because it has been shown that carbinolamides are intermediates in the enzyme mediated synthesis of a-amidated peptides. However, very little systematic work on the reaction of carbinolamides has been completed and even less is known about methods to catalyze the breakdown of these compounds. We propose the study of the reaction of various carbinolamides under aqueous conditions and the factors that catalyze their breakdown. The second area of current interest is the electrophilicity of amides, that is, how susceptible are amides to nucleophilic attack by a carbanion. Shown in Scheme 2 is the general reaction in which we are interested. The reaction proceeds by the formation of an enolate which can then nucleophilically attack the amide to form 2. Compound 2 will then undergo breakdown to form products. There are many interesting aspects to this reaction, the first of which is the reaction itself. We are familiar with similar reactions of this type (eg. Aldol, Claisen, Dieckmann) but this particular reaction has itself received little or no attention. Secondly, by investigating this reaction we will generate data that will allow us to make conclusions about the electrophilicity of amides that may eventually allow a better understanding of resonance. We propose the study of the mixed-Claisen condensation reaction above to determine the nature of this reaction and gain insight into the electrophilicity of amides. In addition, by changing the R groups on nitrogen we may be able to measure changes in the electrophilicity of the amide. Skills and Techniques of Importance: Students (undergraduate and graduate) who work in my labs will receive a variety of experiences: synthesis and purification of organic compounds learn the proper techniques for the determination and analysis of kinetic data and then put these techniques to use learn the operation of analytical instrumentation for the purposes of isolation and identification of reaction products spectral identification of organic compounds and become familiar with methods of obtaining said spectra

Ph D Organic Chemistry

University of Alberta
Edmonton, AB, Canada

BS Science

Brandon University
Brandon, MB, Canada

NSERC Post-Graduate Scholarship

1989

University of Alberta Graduate Faculty Fellowship

1989

NSERC Post-Graduate Scholarship

1988

University of Alberta Graduate Faculty Fellowship

1988

Journal Article

Cope, S., Tailor, D., & Nagorski, R. Determination of the pKa of Cyclobutanone: Bronsted Correlation of the General-Base Catalyzed Enolization in Aqueous Solution and the Effect of Ring-Strain. J. Org. Chem. 76 (2011): 380-390.
Sansone, M., Koyanagi, T., Przybyla, D., & Nagorski, R. Solvent-free synthesis of monoacylaminals from the reaction of amides and aminals as precursors in carbinolamide synthesis. Tetrahedron Lett. 51 (2010): 6031-6033.
Murphy, J., Tenn III, W., Labuda, J., & Nagorski, R. Rapid Amidic Hydrolysis: A Competitive Reaction Pathway Under Basic Conditions for N- (Hydroxymethyl)benzamide Derivatives Bearing Electron-Donating Groups. Tetrahedron Lett. 50 (2009): 7358-7361.
Ankem, R., Murphy, J., & Nagorski, R. Rate of Formation of N-(Hydroxymethyl)benzamide Derivatives in Water as a Function of pH and Their Equilibrium Constants. Tetrahedron Lett. 49 (2008): 6547-6549.
Tenn III, W., Murphy, J., Bim-Merle, J., Brown, J., Junia, A., Price, M., & Nagorski, R. Amidates as Leaving Groups: Structure/Reactivity Correlation of the Hydroxide Dependent E1cB-Like Breakdown of Carbinolamides in Aqueous Solution. J. Org. Chem. 72 (2007): 6075-6083.

Presentations

N-(Hydroxybenzyl)benzamides: pH-Rate Profiles and Zn2+ Catalysis of their Breakdown in H2O. 42nd Meeting of the American Chemical Society Central Region. ACS. (2011)
Non-linear Hammett Correlation for the Hydroxide-Dependent Breakdown of Aromatic Substituted N-(Hydroxybenzyl)acetamides. 42nd Meeting of the American Chemical Society Central Region. ACS. (2011)
Synthesis of N-(-Alkoxybenzyl)amide Derivatives and Initial pH-Dependent Rate Studies in H2O. 42nd Meeting of the American Chemical Society Central Region. ACS. (2011)
The Synthesis and Characterization of N-(- Alkoxybenzyl)acetamides. Illinois State University Undergraduate Research Symposium. Illilnois State University Undergraduate Research Symposium. (2011)
-Hydroxyhippuric Acid Derivatives: pH-Dependent Aqueous Kinetics and Buffer Catalysis. 42nd Meeting of the American Chemical Society Central Region. ACS. (2011)
N-(Hydroxybenzyl)benzamide Derivatives: Hydroxide- Dependent Breakdown and Correlation to the pH-Rate Profiles. Illinois State University Research Symposium. Illinois State University Research Symposium. (2010)
Ring Strain and Its Effect on the Rate of Enolization of Strained and Unstrained Cyclic Ketones and the Correlation of the Brønsted - value to the Ring Size. Illinois State University Research Symposium. Illinois State University Research Symposium. (2010)
The Synthesis and Characterization of N- (Alkoxybenzyl)acetamide Derivatives. Illinois State University Chemistry Club Spring Research Symposium. Illinois State University. (2010)
The Synthesis and Characterization of N-(Alkoxybenzyl)acetamide Derivatives. Illinois State University Undergraduate Research Symposium. Illilnois State University Undergraduate Research Symposium. (2010)
Amidic Hydrolysis: A Competitive Reaction for the Breakdown of Some N- (Hydroxymethyl)benzamide Derivatives Under Basic Conditions. 37th Ontario-Quebec Physical Organic Mini-Symposium. University of Buffalo, SUNY. (2009)

Grants & Contracts

Carbinolamides and N-(Hydroxybenzyl)urea Derivatives: Structure/Reactivity Correlations and Catalysis of the Aqueous Reaction. National Science Foundation. Federal. (2005)
Ring Strain and Antiaromaticity: Their Effect on the Generation and Reactivity of Enolates in Small-Ringed Ketones. American Chemical Society-Petroleum Research Fund, Type B. Federal. (2004)
Determination of the pKa of Benzocyclobutenone. Summer Faculty Fellowship (Illinois State University). Illinois State University. (2002)
Metal-Ion and General Buffer Catalysis of the Aqueous Reaction of N- (Hydroxymethyl)benzamide as a Model for Enzymatic Catalysis. Research Cooporation. Federal. (2002)
Carbinolamides: Reaction and Catalytic Studies in Water. Pre-tenure Faculty Initiative Grant (Illinois State University). Illinois State University. (2001)