Organic Chemistry Print

The organic chemistry subdiscipline at McMaster covers the five major areas or organic chemistry: synthetic, physical organic, bioorganic, polymer and photochemistry. In addition, much of the research in our department involves the application of organic chemistry to problems in other areas of organic chemistry to problems in other areas of science. This is reflected in the number of interdisciplinary research programmes that are being carried out jointly with groups in biochemistry, medicine, physics, and chemical engineering.

    • html Adronov, Alex
      (Synthesis of novel polymer architectures; carbon nanotube functionalization; supramolecular polymer chemistry)
    • html Brook, Michael A.
      (Organosilicon chemistry; polymer chemistry)
    • html Capretta, Fred
      (Organic synthesis and medicinal chemistry, parallel synthesis, chemical biology, transition metal catalysis)
    • html Harrison, Paul H.M.
      (Bioorganic chemistry; biosynthetic processes; biomimetics)
    • html Leigh, William J.
      (Photochemistry; group 14 reactive intermediates)
    • html McNulty, James
      (Synthesis; organophosphine chemistry; anticancer drugs; chemical biology; natural product isolation)
    • html Stöver, Harald D.H.
      (Functional polymers; colloids and microspheres)
    • html Valliant, John F.
      (Medicinal inorganic and radiopharmaceutical chemistry)

 

Synthetic Organic Chemistry involves the laboratory synthesis of specific molecules such as natural products and magnetic resonance imaging reagents. As well, we are interested in the development of new reagents or synthetic techniques that allow highly regio- or stereospecific transformations. Examples of this type of activity include the use of enzymes in organic synthesis and the development of organosilicon compounds as synthetic reagents.

Physical Organic Chemistry is concerned with the structure of organic molecules, and with the mechanisms of chemical reactions. Studies in this field usually combine several different types of experiments. With kinetic measurements we study the effects of substituents, isotopes, and solvent on reaction rates. Possible reactive intermediates such as free radicals, carbenes, or carbenium ions can often be detected directly using sophisticated spectroscopic techniques. The methods employed at McMaster include transient photoelectron spectroscopy, matrix isolation UV and FT-IR spectroscopy, nanosecond laser flash photolysis, electron spin resonance (ESR) spectroscopy, multinuclear solids/liquids NMR spectroscopy, and various forms of tandem mass spectrometry including Neutralization-Reionization Mass Spectrometry (NRMS). These studies give valuable information on the structure, electronic properties, and reactivity of reaction intermediates, and form a cornerstone of physical organic research at McMaster.

Physical Organic Chemistry is concerned with the structure of organic molecules, and with the mechanisms of chemical reactions. Studies in this field usually combine several different types of experiments. With kinetic measurements we study the effects of substituents, isotopes, and solvent on reaction rates. Possible reactive intermediates such as free radicals, carbenes, or carbenium ions can often be detected directly using sophisticated spectroscopic techniques. The methods employed at McMaster include transient photoelectron spectroscopy, matrix isolation UV and FT-IR spectroscopy, nanosecond laser flash photolysis, electron spin resonance (ESR) spectroscopy, multinuclear solids/liquids NMR spectroscopy, and various forms of tandem mass spectrometry including Neutralization-Reionization Mass Spectrometry (NRMS). These studies give valuable information on the structure, electronic properties, and reactivity of reaction intermediates, and form a cornerstone of physical organic research at McMaster.

To confirm and sometimes even predict experimental results, we make use of molecular modelling, semi-empirical and ab initio MO theory calculations. Our department is one of the best-equipped in the country for computer-assisted studies of these types.

Photochemistry, or the chemistry of electronically excited states, deals with the behaviour of molecules upon absorption of light. Practical applications of research in this area abound in everyday life, from the natural processes of plant growth, vision or bioluminescence to artificial ones such as photography or xerography. At McMaster we deal with fundamental as well as applied aspects of mechanistic organic photochemistry, using state-of-the-art facilities for absorption and emission spectroscopy, nanosecond laser flash photolysis, and routine photochemical work in the gas, solution, or solid phases. McMaster is the home of pioneering studies of the photochemistry of carbenium ions, and current research in photochemical pericyclic reactions at McMaster is reshaping the application of orbital symmetry selection rules to excited state reactions. In other work we use well-characterized photochemical reactions or excited state processes to probe the effects of organized media such as liquid crystals, inclusion compounds, and micelles on molecular mobility, or to design special materials such as piezodialysis membranes.

Bio-organic Chemistry encompasses several areas of study. One of these concerns the chemical compounds which occur in nature and their isolation, structure, reactions, and synthesis. Another investigates the biosynthesis of these compounds - elucidation of the pathways by which key molecules are synthesized in biological systems. Such pathways are studied within the living tissues - typically cultures - in which they are found by establishing precursor-product relationships, often by the use of isotopic tracer methods. Alternatively, individual enzyme-catalyzed steps of such pathways may be studied with isolated enzyme preparations. Kinetic and stereochemical aspects of such enzymic reactions comprise one of the major objectives of our current research. Still another area of bio-organic chemistry concerns structure-activity relationships between organic molecules and biologically active macromolecules. Studies of such relationships may lead to an understanding of the mode of action of drugs and of macromolecules in biological environments.

Polymer Chemistry at McMaster involves design, synthesis and characterization of novel monomers and polymers. Rooted in organic preparative chemistry, our graduate students and researchers often translate basic chemistry into polymeric materials that have interesting scientific and industrial properties. Some of our key research efforts involve the preparation of highly efficient polymeric pervaporation membranes that aid in the removal of hydrocarbons from water, and the development of new shape-selective or photoactivated separation membranes. In other projects we develop complex three-dimensional macromolecular structures using a number of different polymerization methods. Two very exciting new fields of research are the selective chemical modification of polymers, and NMR studies of polymer networks and polymer-solvent interactions. All of these studies require a combination of fundamental organic chemistry with an insight into polymer-specific properties. Polymer chemists in our department participate actively in the Brockhouse Institute for Materials Research (BIMR) and in the McMaster Institute for Polymer Production Technology (MIPPT). Collaboration with scientists in other departments such as chemical engineering and in industry help our students gain some perspective on the applications of their research.