Report on the 87th Canadian Chemistry Conference and Exhibition.
The 87th Canadian Chemistry Conference and Exhibition "opened" after a full day of oral presentations and a poster session that included the Undergraduate Students Poster Competition. Richard N. Zare of Stanford University was the Plenary Speaker and discussed the topic of Examining the Ultra Small. Approximately 1,000 people attended this session as well as the Opening Mixer that followed. The London Convention Centre and the adjacent London Hilton Hotel were the sites of this very successful Conference that attracted more than 1,800 attendees from Canada, the U.S. and the rest of the scientific world.
In addition to the long-standing annual all-conference events--the presentation of the CIC Medal lecture by Mitchell A. Winnik of the University of Toronto and the presentation of the Montreal Medal lecture by Tristram Chivers of the University of Calgary--there was an additional all-conference event. A Science Policy Forum was initiated; the Role and Mandate of the National Science Advisor to the Prime Minister was presented by Arthur J. Carty who was appointed National Science Advisor to the Prime Minister in April 2004. From his unique and unprecedemed position, Carty gave an outline of the mandate and responsibilities of his position as well as the immediate and long-range priorities of the role. Time constraints, unfortunately, limited the discussion of this fascinating topic.
There was a CIC Chair's Event, a Green Chemistry and Engineering Forum that was designed to promote awareness in sustainable chemistry and engineering by chemists and chemical engineers with diverse backgrounds. This program was moderated by Sundar Sundararajan, FCIC, then Vice-Chair of the CIC, and addressed topics to encourage the use of better process design to decrease emissions and waste rather than simply using "end-of-the-pipe" solutions. Participants in this timely forum included C. J. Li, McGill University, Joseph Cunningham, Industry Canada, Dave Schwass, NOVA Chemicals and Yves Deslandes, NRC.
In the Chemical Education Division, a standing-room-only audience attended NO, the collaborative production of Carl Djerassi and Pierre Laszlo, which was presented as a word play by three students with accompanying audiovisual support. The subject was a discussion on how to raise money for research on the biological applications of NO and was designed to demonstrate the critical role of chemistry in the interdisciplinary nature of contemporary research. The presentation, which was designed to fit into a classroom setting, was followed by an assessment by Michael Atkinson, one of the University of Western Ontario's (UWO's) 3M Teaching Awardees, and a commentary by one of the playwrights, Pierre Laszlo.
In the usual format of a CSC conference, ten divisions were represented; the History of Chemistry was included with the Chemical Education Division. There were 47 symposia including 10 symposia joint between two divisions as well as seven general sessions and three combined poster sessions.
Front row: Michael Kerr, organizer, Emerging Organic Synthesis: James Wisner, organizer, Self-Assembly and Molecular Recognition: Rob Lipson, conference chair and organizer, Spectroscopy 100 Years after the Birth of Gerhard Herzberg; Kim Baines, scientific program chair; Martin Stillman, divisional rep. of the Environment Division and co-organizer, Teaching Environmental and Green Chemistry and Environmental Science, and organizer, Properties and Functions of Metal Ions and Complexes in Biological Systems; Tom Woo, graduate student program coordinator, divisional rep., Physical and Theoretical Division and co-organizer, Frontiers in Quantum Chemical Modeling and Simulation.
Second row: Zhifeng Ding, organizer, Electrochemistry; Robert Hudson, divisional rep., Biological/Medicinal Chemistry Division, organizer, Frontiers in Nucleic Acid Chemistry; Myra Gordon, communications with authors and Web site liaison; Mel Usselman, divisional rep., History of Chemistry; organizer, all History of Chemistry symposia; Mark Workentin, divisional rep., Organic Chemistry Division.
Third row: Lars Konermann, divisional rep., Analytical Chemistry Division; Keith Griffiths, volunteers coordinator; Peter Guthrie, organizer, Mechanistic Studies in Organic, Biological and Medicinal Chemistry.
Missing from photo: Colin Baird, divisional rep., Chemical Education Division, organizer, all Chemical Education symposia and co-organizer, Teaching Environmental and Green Chemistry and Environmental Science; Michael Bancroft, organizer, Science Capabilities at the Canadian Light Source; Paul Charpentier, divisional rep., Macromolecular Science and Engineering Division; Stella Constas, co-organizer, Classical and Quantum Approaches of Rare Event Dynamics in Condensed-Phase Systems; John Corrigan, divisional rep., Inorganic Chemistry Division; Yining Huang, treasurer and co-organizer, Frontiers in Solid State Magnetic Resonance and co-organizer, Advances in Nuclear Magnetic Resonance Spectroscopy; Peter Norton, divisional rep., Materials Chemistry Division; T.K. Sham, organizer, Materials Science Using Synchrotron Radiation; Ken Yeung, undergraduate student program coordinator and co-organizer, Separations and Bioanalytical Chemistry.
Myra Gordon, MCIC
It has always been difficult to keep up with Richard Zare's research interests. To spectroscopists he was one of the first and most prominent advocates for the use of lasers in spectroscopy and molecular dynamics. His 1970s work on laser-induced fluorescence and reaction dynamics set the pace for a generation of physical chemists and molecular physicists. His recent work on microfluidics and in particular single-cell manipulation and analysis will likely affect analytical chemists in much the same way as Plenary speaker Richard N. Zare his continuing work in molecular physics has influenced laser physics for three decades.
In the opening lecture of the conference entitled, "Adventures in Chemical Analysis," Zare, the Marguerite Blake Wilbur Professor in Natural Science at Stanford University, described the fabrication and functionalization of packed capillary columns having micron-sized pores using sol-gel technology. This monolithic silica structure was used to immobilize the enzyme trypsin that was then used to digest N-benzoyl-L-arginine ethyl ester (BAEE). The reaction took place within the few seconds it took to flow the sample through the column, with an enzymatic activity of 11,000 U, orders of magnitude higher than the activity of free trypsin in solution. Zare attributed the enhanced activity to the much more efficient use of the immobilized enzyme in a forced flow reactor.
[FIGURE 1 OMITTED]
The theme of making things more efficient, cheaper, and smarter continued with the presentation of the Hadamard transform time-of flight mass spectrometer, a regular TOF-MS equipped with a fast shutter for an incoming continuous ion beam. By modulating the shutter at rates that are fast compared to the flight time, and then demodulating the resultant ion signal, Zare showed that the signal-to-noise ratio obtained far exceeded any regular TOF-MS. The advantage of the Hadamard transform TOF is twofold: by being run continuously it can be readily attached to a variety of analytical separation devices, and by having a duty cycle of 50 percent its S/N ratio is superior to a regular TOF-MS.
The remainder of Zare's presentation was a rollercoaster ride in single-cell manipulation and analysis. In a presentation that was animated in every respect, it was shown how "labs-on-a-chip" can be used to trap single cells, to lyse them, to fluorescently label the contents, and to analyze them on columns with only centimetre lengths. The message was clearly that the information obtained by analyzing an ensemble of cells is no more than an average and the contribution from a single cell may be greatly different than the average value. Obviously, the Zare lab is again playing a leading role--this time in the development of microfluidic techniques and single-cell chemical cytometry!
In the Emerging Organic Synthesis Symposium, graduate student Ian Young, ACIC, presented work he has carried out with Michael Kerr, MCIC, at the University of Western Ontario in the development of a new cycloaddition reaction, in which nitrones and cyclopropanes are coupled to make highly functionalized heterocycles. Young showed that the combination of a hydroxylamine 1, aldehyde 2 and cyclopropane 3 produces substituted tetrahydro-1,2-oxazines 5 via the in situ generation of a nitrone 4. The reactions proceed in high yields with near complete diastereoselectivity. The tetrahydro-1,2-oxazine ring is a key structural element of the anti-cancer compound FR900482 7. Using this reaction, a series of FR900482 structural analogs 6 were constructed in only two steps. In addition, a tetrahydro-1,2-oxazine precursor to the tricyclic core of Nakadomarin A 13 has been prepared in a short reaction sequence from 11, the cycloadduct resulting from the coupling of 8, 9, and 10 (See Scheme 1). Current efforts are directed towards the preparation of this highly complex natural product.
Also in Michael Kerr's emerging organic synthesis symposium, Peter Wilson, MCIC, of the department of chemistry at Simon Fraser University described a number of total syntheses that his group has accomplished, including an elegant synthesis of the complete polycyclic ring system of the anti-inflammatory agent artocarpol A (18) (Scheme 2). The synthesis begins by the reaction of 14 with aldehyde 15 to provide cross-condensation products 16 (EE and EZ) as well as the desired 2H-pyran 17 (Scheme 2). 16 was recycled to afford 17 in a combined overall yield of 70 percent. Irradiation of a dilute solution of 17 in the presence of benzophenone gave the artocarpol A analog 18 in 45 percent yield in an amazingly direct synthetic pathway.
In the Spectroscopy 100 Years After the Birth of Gerhard Herzberg Symposium organized by Rob Lipson, MCIC, Benoit Simard, MCIC (group leader, molecular spectroscopy, Steacie Institute, NRC), presented an invited talk focusing on three issues of current importance to gas phase molecular spectroscopy. The talk began with the seemingly simple but unassigned Resonant 2-Photon Ionization (R2PI) spectrum of the linear Si-N-Si molecule. He showed that in this case, laser-induced fluorescence and dispersion emission spectroscopy were better suited to study the molecule and in fact the visible spectrum can be assigned unambiguously. He then demonstrated that it was possible to obtain high-quality Stimulated Emission Pumping (SEP) spectra in noisy environments such as those found in laser vaporization sources, plasmas, and possible flames. As an example he used the visible spectrum of PH2 generated in a laser vaporization source. Finally, he showed that Infrared Multi-Photon Depletion spectroscopy with a continuous free-electron laser beam is a powerful tool to probe the structure and bonding of ligated metal clusters such as [Rh.sub.n]-CO(n = 2-30).
In the Main Group Chemistry Symposium organized by Ignacio Vargas-Baca, MCIC, and Charles Macdonald, MCIC, the chemistry of phosphoranimines X[R.sub.2]P = NSi[Me.sub.3] (X = Cl, Br, OC[H.sub.2]C[F.sub.3], etc.) was described by graduate student Keith Huynh, MCIC. These compounds are of considerable interest because they possess phosphorus-nitrogen multiple bonds and would be convenient precursors to high molecular weight polyphosphazenes. Phosphoranimine cations [[R.sub.2]P = NSi[Me.sub.3]] + have been considered as key intermediate species in the polymerization mechanism. To date, attempts to generate transient cationic species of this type have been unsuccessful. However, in recent research described during the talk, which was performed together with fellow graduate student Eric Rivard, MCIC, in Ian Manners, FCIC's, group at the University of Toronto, the presence of a strong donor ligand (L) such as 4-dimethylaminopyridine has been found to allow the labile cations to be isolated and fully characterized (Scheme 3). The resulting donor-stabilized phosphoranimine cations [L[R.sub.2]P [equivalent to] NSi[Me.sub.3]] + showed extensive shortening of the PN bond (down to 1.46 - 1.49 [Angstrom]) and widening of the angle at nitrogen (up to 144-173[degrees]) compared to the neutral phosphoranimine precursors and possess what can be considered to be phosphorus-nitrogen bonds with significant triple bond character. Efforts to prepare the analogous phosphine stabilized cations [L[R.sub.2]P [equivalent to] NSi[Me.sub.3]] + (L = phosphine) resulted in imine transfer, which provided a convenient route to tri-organo-substituted phosphoranimines without the use of hazardous azides (J. Am. Chem. Soc. 2004, 126, 2286).
In the Scanning Probe Microscopy Symposium organized by John-Bruce Green, MCIC, Gregory Lopinski, MCIC, from the Steacie Institute, NRC, gave an invited talk on the chemical modification of silicon surfaces for applications in conventional microelectronics and in the fabrication of novel hybrid organic/silicon molecular devices and sensors. Atomically flat hydrogen terminated Si(111) (produced via a wet chemical etching process) is being used by a number of groups to produce surfaces terminated with halogens as well as with a wide range of organic functional groups and biomolecules. On surfaces of semiconductors such as silicon, adsorption of electron donating or withdrawing species can lead to long-range band-bending effects that alter the conductivity of the underlying substrate. The Lopinski group demonstrated that chlorination of n-type H/Si(111) surfaces leads to a significant increase in the surface conductivity that can be attributed to the formation of a minority carrier channel resulting from the electron withdrawing nature of the chemisorbed chlorine. By using conductivity as an in-situ probe of the gas phase reaction of molecular chlorine with H/Si(111), they observed that this reaction could take place spontaneously in the dark at room temperature, while previous chlorination reactions used UV light of elevated temperatures. Under the mild reaction conditions used here, the resulting surfaces have very low defect densities. See the STM image in Figure 2. The Si-Cl stretch is also observed in high-resolution electron energy loss spectroscopy (HREELS) measurements. High-quality halogenated surfaces made by this approach may prove useful to form hydroxylated surfaces for growth of high k dielectric layers for microelectronic applications. Alternately they can be used as a more reactive alternative to the H-terminated surface for the covalent attachment of organic molecular layers to silicon. On-going work involves exploring reactions of a wide range of molecules with these surfaces, using conductivity to monitor the reactions and HREELS and STM to characterize the resulting surfaces.
[FIGURE 2 OMITTED]
In the Photoprocesses in Molecular Assemblies Symposium organized by David Andrews, Christopher Barrett, MCIC, from McGill University described his group's research into self-assembled photo switches. His approach involves the preparation of multilayer thin films of polyelectrolytes incorporating azobenzene, which switches between cis and trans forms depending on the frequency of light with which it is irradiated. In other words, it is "photo-responsive." A variety of photo-responsive polymeric materials including homopolymers, statistical copolymers, and block copolymers were studied with an eye towards understanding how light influences the surface and structural properties of the materials. Many potention applications of the azo-polyelectrolytes were described, including their use as sensors, for signal processing or information storage and for light-activated drug delivery.
Scott Maybury from the University of Toronto presented a lecture in the Environmental Analytical Chemistry Symposium organized by Renata Bailey, MCIC, describing his research into the bioaccumulation of toxins. Human and animal tissues collected in urban and remote global locations contain persistent and bioaccumulative perfluorinated carboxylic acids (PFCAs). The source of PFCAs was previously unknown. The talk presented smog-chamber studies that indicate fluorotelomer alcohols (FTOHs) can degrade in the atmosphere to yield a homologous series of PECAs. Atmospheric degradation of FTOHs is likely to contribute to the widespread dissemination of PECAs. After accounting for their bioaccumulation potential, the pattern of PECAs yielded from FTOHs could account for the distinct contamination profile of PFCAs observed in arctic animals. Furthermore, polar bear liver was shown to contain predominately linear isomers (> 99 percent) of perfluorononanoic acid (PENA) while both branched and linear were observed for perfluorooctanoic acid, strongly suggesting a sole input of PENA from "Telomer" based products. The significance of the gas-phase acyl peroxy radical cross-reactions that produce PECAs has not been previously recognized. Such reactions are expected to occur during the atmospheric degradation of all polyfluorinated materials, necessitating a re-examination of the environmental fate and impact of this important class of industrial chemicals.
Helen P. Graves Smith, MCIC, of the Canada Science and Technology Museum in Ottawa, ON, gave a presentation in the Chemical Education Division "Canadian Firsts" organized by Mel Usselman describing the life of Raymond Urgel Lemieux (1920-2000). Lemieux is one of the newest members of the Canadian Science and Engineering Hall of Fame. His contributions in the field of carbohydrate chemistry earned him worldwide recognition, including his monumental total synthesis of sucrose, reported for the first time in 1953. Lemieux joins other notable chemists including John Polanyi, E.W.R. (Ned) Steacie, and Michael Smith.
Ray Lemieux was a man who believed that "being in the academe gives one the opportunity to do the kind of research in which discoveries made along the way will prove more important than the initial goals set for the research program." He also said, in his 1990 book, Explorations with Sugars: How Sweet It Was, that he owed his career to "the trust placed in [him] by [his] family and employers."
The induction ceremony for the Hall of Fame took place at the Museum in Ottawa on May 20, 2004. Ray's wife and several of their children and friends traveled from Alberta, the U.S., and elsewhere to be there to share in the event. Photos taken that evening were included in the presentation, which also included proton NMR spectra of sucrose at 90 MHz and 600 MHz, generously provided by D. R. Bundle, A. Otter, and C. C. Ling (University of Alberta).
Cathleen Crudden, MCIC
Hans-Peter Loock, MCIC
CSC Conference at a Glance
Exhibitor Aida Krneta of John Wiley & Sons Canada Ltd.
Martin Tanner, MCIC, claims his Merck Frosst Award.
Info is exchanged at the Sigma-Aldrich booth.
Margaret-Ann Armour, FCIC, poses with Reg Friesen Award winners.
The Montreal Award is bestowed upon Tris Chivers, FCIC.
Undergraduate Student Award winners smile for the camera.
Dick Puddephatt, FCIC, presents the CIC Medal to Mitchell Winnik, MCIC.
Sundar Sundararajan, FCIC, receives the NOVA Chemicals Award.
Eugenia Kumacheva, MCIC, receives her Clara Benson Award.
Conference goers enjoy the opening reception.
Seven universities had a successful day at the CSC Graduate Studies Fair.
The Canadian Society for Chemistry wishes to thank the members of the organizing committee, the conference sponsors, and volunteers for creating a well planned, successful conference.
Robert Lipson, MCIC, Conference Chair
Kim Baines, FCIC, Scientific Program Chair
Myra Gordon, Communications with Authors, Web site Liaison
Yining Huang, MCIC, Treasurer
Tom Woo, MCIC, Graduate Student Program Coordinator
Ken Yeung, MCIC, Undergraduae Student Program Coordinator
Keith Griffiths, MCIC, Volunteers Coordinator
Rita Afeltra, Logistics, CIC/CSC Liaison, Social Activities, Exhibition
Roland Andersson, MCIC, CIC Executive Director
Joan Kingston, CIC Director, Finance and Administration
Pierre Lemasson, MCIC, Technical Support
Cheryle Levert, Communications, Marketing, Media Relations
Gale Thirlwall-Wilbee, Awards, Career and Graduate Studies Fair
($10,000 and Up)
* 3M Canada
* AstraZeneca Canada Inc.
* Bruker Canada
* Canadian Light Source, University of Saskatchewan
* University of Western Ontario, department of chemistry
* Advanced Chemistry Development, Inc. (ACD/Labs)
* Agilent Technologies
* Applied Biosystems
* Boehringer Ingelheim (Canada) Ltd.
* Brantford Chemicals Inc./Apotex Pharmachem Inc.
* Bristol-Myers Squibb Canada
* Dalton Chemical Laboratories Inc.
* Eli Lilly Cariada Inc.
* Department of Chemistry and Biochemistry, University of Guelph
* GlaxoSmithKline Inc. Canada
* Hudson Research Group
* Ionalytics Corporation
* MAKerr Laboratories
* MBraun USA
* Merck Frosst Canada Ltd.
* Merck Frosst Centre for Therapeutic Research
* PENCE Inc.
* Perkin Elmer Canada
* Petroleum Research Fund
* Pfizer Inc.
* Smart & Biggar
* Strem Chemicals, Inc.
* University of Western Ontario, Faculty of Science
* University of Western Ontario, VP Research
* Varian Canada, Inc.
* VWR International
* Waters Canada
* Wellington Laboratories
* Wiley Canada
* Xerox Research Centre of Canada
(Up to $1,000)
* Aegera Therapeutics Inc.
* Affinium[TM] Pharmaceuticals
* American Dye Source, Inc.
* Apotex Inc.
* C/D/N Isotopes
* Chromatographic Specialties Inc.
* College of Physical and Engineering Sciences, University of Guelph
* Hoffmann-LaRoche Inc.
* Malvern Instruments
* Mandel Scientific
* McDonald's Canada
* NOVA Chemicals
* Pearson Education Canada
* Random House of Canada Limited
* Seastar Chemicals Inc
* Spectra Research Corporation
* STOE & Cie GmbH
* SynFine Research, Inc.
* Torcan Chemical Ltd.
* Thomson Nelson
* W.H. Freeman
Anasazi Instruments Inc.
Bruker Biospin, Daltonics and Optics
Canadian Light Source Inc.
Cedarlane Laboratories Inc.
Chemical Abstracts Service
FTS Systems Canada
Gamble Technologies Ltd.
Hayden-McNeil Specialty Products
John Wiley & Sons Canada, Ltd.
Lasalle Scientific Inc.
London Scientific Limited
M. Braun Inc.
McGraw-Hill Ryerson Ltd.
Merck Frosst Canada
M R Resources, Inc.
NRC Research Press--National Research Council Canada
P & P Optica
Pearson Education Canada
Photon Technology International
Rose Scientific Ltd.
Royal Society of Chemistry
Spectra Research Corporation
Strem Chemicals, Inc.
Systems for Research Corporation
The Blueprint Initiative
Thomson Nelson Learning
Vacuum Atmospheres Company
Thanks to all who made the 87th Canadian Chemistry Conference and Exhibition a success. See you next year ... in Saskatoon!
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|Title Annotation:||CSC Bulletin SCC|
|Publication:||Canadian Chemical News|
|Date:||Nov 1, 2004|
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