Chemistry, Saint Mary's University

Chemistry

Faculty

Robert D. Singer
Professor

B.Sc. (Saint Mary's University)
Ph.D. (Simon Fraser)
Alexander von Humboldt Fellow (Universität Marburg, Germany)
Father William Stewart S.J. Medal for Excellence in Teaching, Saint Mary's University, 1999

Honorary Associate, Victorian College of Pharmacy, Monash University 2007 – 2010

Contact: Robert Singer

Biographical Sketch

Dr. Singer, a native Nova Scotian, obtained his B.Sc. Honours (First Class) at Saint Mary's University in 1986. He went on to obtain a Ph.D. in Organic Chemistry with an NSERC PGS Award at Simon Fraser University under the supervision of Professor A. C. Oehlschlager. Upon a successful thesis defense in 1992, he took up an Alexander von Humboldt Fellowship at the Universität Marburg in Germany under the supervision of Professor Paul Knochel until September 1993 when he took up an Assistant Professor position at his alma mater. He is now a Full Professor and has served as the Chair of the Department of Chemistry at Saint Mary's University and on the University's Academic Senate and Board of Governors.

Research Interests

Green Chemistry, Ionic Liquids as Reaction Media,
Organometallic Methodology, Asymmetric Synthesis

General:

Since becoming a faculty member in the department of Chemistry at Saint Mary's University Dr. Singer has employed over 60 undergraduate research assistants including 15 Honours students, 3 Masters students and a Doctoral student. He has attracted over 3 million dollars of funding for his research from a variety of internal and external sources including NSERC, PRF, CFI, Pfizer Pharmaceutical, Glaxo-Smith-Kline Australia, and PRAC. His current research interests lie in the filed of Green Chemistry with particular emphasis on Ionic Liquids as Neoteric Solvents. This area of interest is complemented by his research in Organometallic Reagents in Organic Synthesis and Synthetic Methodology.

Summary of current interests:

The development of “Green Chemistry”, or environmentally benign chemistry, is an area of increasing significance in today's society. Green Chemistry is aimed at the reduction or elimination of hazardous substances in the design, manufacture and application of chemical products. These goals can be achieved, in part, by increasing reaction yields, rates, and selectivities. Other key components of any “green” process include the ability to recycle and reuse unused reactants, catalysts and solvents while avoiding release of harmful volatile organic compounds (VOC's).

Room Temperature Ionic Liquids (RTIL's) are a new class of polar, non-coordinating solvents that are typically composed of an organic cation and an inorganic anion and are liquids at or below room temperature. Our group is concerned with the exploitation of the beneficial “green” properties of these inherently non-volatile solvents. As such, our overall program can be divided into four sub-categories: (1) The design, synthesis, and characterization of new ionic liquids capable of acting as novel reaction media and/or extractants.; (2) Development of RTIL–metal complexes that have potential as easily recycled, immobilized homogeneous catalysts for important organic reactions.; (3) Adaptation of bimetallic addition reactions to RTIL systems. Early studies in our laboratory indicate increased selectivites and product yields using RTIL's in reactions of bimetallic reagents with unsaturated organic substrates. Furthermore, we have shown that catalysts for these reactions can be easily recycled and reused using RTIL's.; (4) Organometallic synthetic methodology development. Our earlier work involving useful zincate reagents, and others, with potential use in asymmetric synthesis will continue. Adaptation of such organometallic reagents to RTIL systems are being conducted.

RTIL's afford novel reaction conditions affording higher yields of single products while being recyclable and reusable. They are excellent candidates for replacements to industrially used solvents and have their highest potential impact in this context.

Links to related research

http://www.chemsoc.org/networks/gcn/index.htm
http://www.greenchemistry.ca/
http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=greenchemistryinstitute/index.html

Current Group

Ted Abraham (Honours), Jeanna MacLeod (Honours), Alwyn Gomez, Kenson Ambrose, Alanna Durand,

Previous Honours Students

Ted Abraham – finishing course requirements
Stephanie Russell – Applying for Grad school
Jeff Farrell – Ph. D. Chemistry (in progress), University of Toronto, Toronto, Ontario; CGS-M
Carrie-Lee Trider – Medical School, Dalhousie University
Amy Holland – M.Sc. Chemistry (in progress) Queen's University, Kingston, Ontario; NSERC-PGS-M
Darrell Dean - Ph. D. Chemistry (in progress), Queen's University, Kingston, Ontario; NSERC-PGS-M
Whitfield Lewis - Industry
Steven Dickson - Ph. D. Chemistry (in progress), Queen's University, Kingston, Ontario
Gavin Beck - Medical School, Dalhousie University
Elizabeth Turner - Ph.D. Chemistry (in progress), University of Western Ontario, NSERC PGS A and CGS-D scholarship winner
Ivan Hemeon - Ph.D. Simon Fraser University (in progress), M.Sc. Applied Science, Saint Mary's University, NSERC PGS A and CGS-D scholarship winner
Jeremy Finden - Ph. D. Organic Chemistry, Queen's University, Kingston, Ontario; NSERC PGS A scholarship winner
Kim Hennigar - MBA, Saint Mary's University
Kevin Kells - Ph. D. Organic Chemistry, University of Waterloo, Waterloo, Ontario; NSERC PGS A and B scholarship winner
Laine Green - M.D., Dalhousie University, M.Sc. Organic Chemistry, Queen's University, Kingston, Ontario; NSERC PGS A and PGS B scholarship winner
Jacqueline K. D. Surette - M.Sc. Leisure Studies, Dalhousie University; NSERC PGS A scholarship winner
Bonnie L. MacLean - M.Sc. Art Conservation, Queens University, Kingston, Ontario; NSERC PGS A scholarship winner
Annegret Stark - Ph.D., Queens University Belfast, 2002
Karla Randell - Ph. D., Simon Fraser, 2000; NSERC PGS A and B scholarship winner
Andrew Vaughan - M.Sc., University of California at San Diego 1996; NSERC PGS A scholarship winner; Alfred Bader Award for Excellence in Organic Chemistry for Honours Thesis; Transcell Technologies, New Jersey, U.S.A.; UPEI Veterinary School, 2001

Teaching

Dr. Singer has taught a wide variety of undergraduate chemistry courses and a selection of graduate level courses in the Masters of Applied Science program. He was awarded the Father William Stewart S.J. Medal for Excellence in TeacAdd to Publications listhing at convocation in May 1999. He is involved in a number of community outreach activities such as annual presentations at the regional high school science teacher's conference, organizing high school tours of the Faculty of Science, the Molecules of Life Elementary School Outreach Program, and lectures at high schools on Green Chemistry. The following is list of courses he has taught:

CHEM1210.1 – General Chemistry I
CHEM1211.2 – General Chemistry II for Physical Sciences
CHEM1212.0 – General Chemistry for Life Sciences
CHEM2344.1 – Organic Chemistry I
CHEM2345.2 – Organic Chemistry IIA
CHEM3443.1 – Organic Reaction Mechanisms
CHEM4444.2 – Synthesis in Organic Chemistry
CHEM3445.2 – Organic Spectroscopy
CHEM4498.0 – Selected Research Topics in Chemistry (Seminar course)
CHEM4500.0 – Research Thesis (Honours)
CHEM6698.0 – Selected Topics in Organic Chemistry
APS6603.0 – Graduate Research Thesis
APS6600.0 – Graduate Seminar
FOR2200.1 – Basic Sciences for Forensics I

Publications

Jitendra R. Harjani, Theodore J. Abraham, Alwyn T. Gomez, M. Teresa Garcia, Robert D. Singer,* and Peter J. Scammells* Submitted to Green Chem. 17-Sep-09 B919394D ”Sonogashira Coupling Reactions in Biodegradable Ionic Liquids Derived from Nicotinic Acid”

Prashant U. Naik, Jeff Farrell, Carrie Lee Trider, Dejan-Kresimir Bucar , Leonard R. MacGillivray and Robert D. Singer* Submitted to Chem. Commun. 6 February 2009, “Synthesis of a bicyclic palladacycle with an abnormal NHC – palladium bond from a Task Specific Ionic Liquid” B902610J

Prashant Naik and Robert D. Singer “Salicylaldoxime and salen containing ionic liquids for metal complexes” PCT Int. Appl. PCT/CA2009/000229; WO 2009/105881.

Farzad Atefi, M. Teresa Garcia, Robert D. Singer*, Peter J. Scammells*, Green Chem. , 2009, 11, 1595 – 1604. “Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability”.

Jitendra R. Harjani, Jeff Farrell, M. Teresa Garcia, Robert D. Singer*, and Peter J. Scammells*, Green Chem. 2009 , 11, 821 - 829 “Further Investigation of the Biodegradability of Imidazolium Ionic Liquids”

Marangoni, Gerrard; Singer, Robert; Singh, Kulbir; Quinn, Jason J. Colloid Interface Sci. 335, (2009), 105 - 111 “Spontaneous Vesicle Formation with an Ionic Liquid Amphiphile”

Jitendra R. Harjani,a Robert D. Singer,b M. Teresa Garciac and Peter J. Scammellsa,* Green Chemistry , 2009, 11, 83 - 90 “Biodegradable Pyridinium Ionic Liquids: Design, Synthesis and Evaluation”

Naik, P. U., Trider, C.L., Farrell, J., Singer, R. D . I & EC ACS Symposium Series , Accepted February 20, 2009 “Ionic Liquid Complexes for Metal Extractions and Biphasic Catalysis”

Prashant U. Naik, Greg McManus, Michael J. Zaworotko and Robert D. Singer* Dalton Trans. 2008, 4834 – 4836. “Salicylaldoxime and salen containing imidazolium ionic liquids for biphasic catalysis and metal extractions”

Jitendra R. Harjani, Prashant Naik, Tomislav Frišcic,, Leonard R MacGillivray, and Robert D. Singer* Dalton Trans. 2008, 4595 – 4601. Inside Cover “Removal of Metal Ions from Aqueous Solutions Using Chelating Task-Specific Ionic Liquids”Miranda L. Cheney, Michael J. Zaworotko, Steven Beaton, and Robert D. Singer* J. Chem. Ed. 2008, 85, 1649 – 1651. “Cocrystal Controlled Solid-State Synthesis – C3S3: A Green Chemistry Experiment for Undergraduate Organic Chemistry” Entered on the Greener Education Materials for Chemists (GEMs) database, March 2009.

Jitendra R. Harjani, Robert D. Singer, M. Teresa Garcia and Peter J. Scammells* Green Chemistry 2008, 10, 436. “The Design and Synthesis of Biodegradable Pyridinium Ionic Liquids”

Teresa Lama, Robert D. Singer and William D. Lubell “Peptides of Life - Teaching Peptide Science and Art in Elementary School” Peptides for Youth, The Proceedings of the 20th American Peptide Symposium, Series: Advances in Experimental Medicine and Biology , Vol. 611, Del Valle, Susan; Escher, Emanuel; Lubell, William D. (Eds.) Springer, 2008.

Prashant Naik and Robert D. Singer “Salicylaldoxime and salen containing ionic liquids for metal complexes” Provisional Patent filed in US Patent and Trademark Office (USPTO), February 28, 2008 application #: 61/032,103.

Sandrine Bouquillon, Thomas Courrant, Darrell Dean, Nicholas Gathergood, Saibh Morrissey , Bruce Pegot , Peter J. Scammells, and Robert D. Singer Aust. J. Chem.. 2007, 60, 843-847. “Biodegradable Ionic Liquids: Selected Applications”

Singer, Robert Douglas; Harjani, Jitendra “Imidazolium-containing amino carboxylate compounds and analogs for complexing metal ions, useful as ionic liquids, for extraction of metals from liquids, and their complexes as catalysts for air purification or organic reactions.” PCT Int. Appl. (2007), 62pp. CODEN: PIXXD2 WO 2007071028 A1 20070628 CAN 147:108436 AN 2007:702731.

Sandrine Bouquillon, Thomas Courrant, Darrell Dean, Nicholas Gathergood, Saibh Morrissey , Bruce Pegot , Peter J. Scammells, and Robert D. Singer “Biodegradable Ionic Liquids: Selected Applications” Tetrahedron Submitted May, 2007.

Miranda L. Cheney, Michael J. Zaworotko, and Robert D. Singer “Cocrystal Controlled Solid-State Synthesis – C3S3: A Green Chemistry Experiment for Undergraduate Organic Chemistry” J. Chem. Ed. Submitted May 22, 2007.

Jitendra R. Harjani, Tomislav Frišcic , , Leonard R. MacGillivray and Robert D. Singer “Removal of Metal Ions from Aqueous Solutions Using a Chelating Ionic Liquid” Inorg. Chem. 2006 ; 45 (25); 10025-10027.

Jitendra Harjani and Robert D. Singer “COMPOUNDS, Complexes AND uses thereof” PCT provisional patent application, 2006 PCT/CA2006/002060.

Jitendra Harjani and Robert D. Singer “Task Specific Ionic Liquids Capable Containing an Ethylamine Diacetic Acid Moiety” US provisional application No. 60/752,880, filed on December 23, 2005 .

Steven Dickson, Darrell Dean, and Robert D. Singer “Silystannations of a,ß-unsaturated carbonyl compounds via the generation of Bu3Sn- in ionic liquids” Chem. Commun. 2005, DOI:10.1039/B508400H.

Peter J. Scammells, Janet L. Scott, Robert D. Singer “Ionic Liquids: The Neglected Issues” Aust. J. Chem. 2005, 58, 155-169. Invited Review.

Riina K. Arvela, Nicholas E. Leadbeater,* Michael S. Sangi, Victoria J. Williams, Patricia Granados, and Robert D. Singer “A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology” J. Org. Chem. 2005, 161-168.

Kristy McCamley, Nick Warner, Peter Scammells, Marc Lamoureux, and Robert D. Singer* “Quantification of chloride ion in dialkylimidazolium tetrafluoroborates using ICP-MS analysis” Green Chem. 2004, 6, 341 – 344.

Ivan Hemeon, Neil W. Barnett, Nicholas Gathergood, Peter J. Scammells, and Robert D. Singer “Manganese Dioxide Allylic and Benzylic Oxidation Reactions in Ionic Liquids” Aus. J. Chem. 2004, 57, 125-128.

Ivan Hemeon and Robert D. Singer* “Recyclable Palladium(0)-Catalysed Silylstannation of Terminal Alkynes in Ionic Liquids” J. Mol. Cat. A 2004, 214, 33-44. Invited Contribution

Kristy McCamley, Justin A. Ripper, Robert D. Singer, Peter J. Scammells* “Efficient N-Demethylation of Opiate Alkaloids using a Modified Non-Classical Polonovski Reaction” J. Org. Chem. 2003, 68, 9847 - 9850.

Jeremy Finden, Gavin Beck, Andrea Lantz, Rosa Walsh, Michael J. Zaworotko, and Robert D. Singer* “Preparation and characterization of 1-butyl-3-methylimidazolium tetrakis(3,5-bis(trifluoromethyl)phenyl) borate, [bmim]BARF” J. Chem. Crystallogr., 2003, 33, 283 - 293.

Elizabeth A. Turner, Cory Pye, and Robert D. Singer* “Use of ab initio calculations towards the rational design of room temperature ionic liquids.” J. Phys. Chem., 2003, 2277 - 2288.

Ivan Hemeon, Steve Dickson, and Robert D. Singer* “Recent advances in the use of ionic liquid solvents based on 1,3-dialkylimidazolium cations in selected organic reactions.” Invited Review to be submitted to Recent Research Developments in Organic Chemistry, 6 (2002): 499 - 519.

Ivan Hemeon and Robert D. Singer, “Silylstannation of terminal alkynes using a recyclable palladium(0) catalyst immobilised in an ionic liquid” Chem. Commun., 2002, 1884 - 1885.

Ivan Hemeon, Carolyn DeAmicis, Hilary Jenkins, Peter Scammells, and Robert D. Singer* ”Endo Selective Diels-Alder Reactions of Furan in Ionic Liquids” Synlett, 2002, 1815 - 1818.

R. D. Singer Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silyllithium Reagents, Volume 4, Chapter 4.4.11, 2002, pg. 237.

R. D. Singer Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silylcopper Reagents, Volume 4, Chapter 4.4.10, 2002, pg. 231.

I. Hemeon and R. D. Singer Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silylzinc Reagents, Volume 4, Chapter 4.4.9, 2002, pg. 225.

I. Hemeon and R. D. Singer Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silylaluminum Reagents, Volume 4, Chapter 4.4.8, 2002, pg. 219.

I. Hemeon and R. D. Singer Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silylboron Reagents, Volume 4, Chapter 4.4.7, 2002, pg. 211.

I. Hemeon and R. D. Singer Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silyltin Reagents, Volume 4, Chapter 4.4.6, 2002, pg. 205.

Robert D. Singer and Peter J. Scammells "Alternative methods for the MnO2 oxidation of codeine methyl ether to thebaine utilizing ionic liquids.” Tetrahedron Letters, 2001, 42: 6831 - 6833.

Scammells, P. J., Ripper, J. A. Singer, R. D., Australian Provisional Patent, PQ9683, 2000 “Novel Syntheses of Commercially Important Opiates.”

Laine Green, Ivan Hemeon, and Robert D. Singer, Tetrahedron Lett. 2000, 41, 1343. “1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as reaction media for the acylative cleavage of ethers.”

Annegret Stark, Bonnie L. MacLean, and Robert D. Singer, J. Chem. Soc., Dalton Transactions 1999, 63 - 66 “1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reactions of ferrocene.”

Kumar Biradha, Robert D. Singer , Annegret Stark, Keith Vaughan and Michael J. Zaworotko, J. Chem. Cryst. 1998, 28, 799 -811 “Crystal structures of 3,7-bis-(arylazo)-1,3,5,7-tetraaza[3.3.1]bicyclononanes.”

Robert D. Singer 42nd Annual Report on ResearchUnder Sponsorship of the Petroleum Research Fund Administered by the American Chemical Society, 1998, 42, 252. “New Organometallic Methodologies.”

Bonnie L. MacLean, Kimberlea A. Hennigar, Kevin W. Kells and Robert D. Singer Tetrahedron Lett., 1997, 38, 7313. “Conjugate Addition of Dimethylphenylsilyllithium to a,ß-Unsaturated Carbonyl Compounds Mediated by Sub-stoichiometric Quantities of Dimethylzinc.”

Jacqueline K. D. Surette, Laine Green, and Robert D. Singer, J. Chem Soc., Chem. Commun., 1996, 2753 "1-Ethyl-3-methylimidazolium haloaluminate melts as reaction media for the Friedel-Crafts acylation of ferrocene."

Andrew Vaughan and Robert D. Singer, Tetrahedron Lett., 1995, 36, 5683. “Conjugate Addition of Zinc Halide Derived-Unsaturated Carbonyl,Trialkylsilyl(dialkyl)zincate Reagents to a,ß Compounds”.

Jacqueline K. D. Surette, Mary-Anne MacDonald, Michael J. Zaworotko, and Robert D. Singer, J. Chem. Crystall., 1994, 24, 715. “X-ray Crystal Structure of 1,4-diphenylbutadiyne”.

Alois Fürstner, Robert Singer, and Paul Knochel, Tetrahedron Lett., 1994, 35, 1047. “A Convenient Preparation of Functionalised Arylzinc Compounds by the Reaction of Zinc/Silver-Graphite with Aryl Iodides”.

Paul Knochel and Robert D. Singer, Chemical Reviews, 1993, 93, 2117. “Preparation and Applications of Polyfunctional Organozinc Reagents in Organic Synthesis”.

Robert D. Singer and Allan C. Oehlschlager, J. Org. Chem., 1992, 57, 2192. “Effect of Coordinating Solvent on Higher Order Organocyanocuprates”.

Robert D. Singer, Michael Werner Hutzinger, and Allan C. Oehlschlager, J. Org. Chem., 1991, 56, 4933. “Additions of CuCN Derived Stannylcuprates to Terminal Alkynes: A Comparative Spectroscopic and Chemical Study”.

Robert D. Singer and Allan C. Oehlschlager, J. Org. Chem., 1991, 56, 3510. “The Composition and Chemistry of the Mixed Higher Order Cuprates (PhMe2Si)m(CH3)nCu(CN)Lim+n”.

Michael Werner Hutzinger, Robert D. Singer, and Allan C. Oehlschlager, J. Am. Chem. Soc., 1990, 112, 9397. “Spectroscopic and Chemical Evidence for the Reversible Formation of Vinylcopper Intermediates in the Stannylcupration of Terminal Alkynes”.

Hugo Klahn-Oliva, Robert D. Singer, James M. Aramini, and Derek Sutton, Inorg. Chem., 1989, 28, 4217. “Synthesis and Cis-Trans Isomerism of (Pentamethylcyclopentadienyl)rhenium(III) Halide Complexes formed by Oxidative Addition of X2 or HX (X = Cl, Br, I) to (?5-C5Me5)Re(CO)2(PMe3) or (h5-C5Me5)Re(CO)(PMe3)(N2)”.

K. Vaughan, K. U. K. Gamage Nicholas, R. D. Singer, M. Roy, and N.W. Gibson, Anti-Cancer Drug Design, 1987, 2, 279. “Triazene Metabolism VI. 3-Azidomethyl-3-alkyl-1-aryltriazenes, A new Class of Anti-Tumour Triazene with Potential Pro-drug Applications”.

Hugo Klahn-Oliva, Robert D. Singer, and Derek Sutton, J. Am. Chem. Soc., 1986, 108, 3107. “The Rhenium Dinitrogen Complex (h5-C5Me5)Re(CO)(PMe3)(N2). Facile Photochemical Generation of a Rhenium Intermediate and Oxidative Addition of Hydrocarbon C-H Bonds”.

Robert D. Singer, Keith Vaughan, and Donald L. Hooper, Can. J. Chem., 1986, 64, 1567. “Open Chain Nitrogen Compounds. Part XI. 3,7-Bis(Arylazo)-1,3,5,7-Tetraazabicyclo-[3.3.1]-Nonanes: The Reaction of Diazonium Ions with Ammonia Formaldehyde Mixtures”.

Seminars and Abstracts

“Synthesis in Biodegradable Ionic Liquids” Jitendra Harjani, Peter J. Scammells, M. Teresa Garcia, Jeff Farrell, and Robert D. Singer 92nd Canadian Chemistry Conference, Hamilton, Canada (05/09) – Invited.

“Cobalt and Nickel Complexes of a Task Specific Ionic Liquid” Stephanie J. Russell and Robert D. Singer; 34th Atlantic CIC Student Conference 2009, Antigonish, N.S. (05/09).

“Formation of a Tridentate Palladium (II) Pincer Complex with an Abnormal Metal-N-Heterocyclic Carbene Bond” Jeff Farrell , Prashant Naik, Carrie-Lee Trider, and Robert D. Singer; 34th Atlantic CIC Student Conference 2009, Antigonish, N.S. (05/09). Awarded Best Inorganic Oral Presentation

“Biodegradable Ionic Liquid Surfactants” Alwyn Gomez , Ted Abraham, and Robert D. Singer, Kulbir Singh, and Gerrard Marangoni; 34th Atlantic CIC Student Conference 2009, Antigonish, N.S. (05/09).

“Synthesis of a bicyclic palladacycle with an abnormal NHC – palladium bond from a Task-Specific Ionic Liquid” Jeff Farrell, Prashant U. Naik, Carrie Lee Trider and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/09).

“Cobalt and Nickel Complexes of a Task Specific Ionic Liquid”, Stephanie J. Russell and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/09).

“Biodegradable Ionic Liquid Surfactants” Alwyn Gomez , Ted Abraham, and Robert D. Singer, Kulbir Singh, and Gerrard Marangoni, Maritime Inorganic Discussion Weekend (03/09).

“Ionic Liquid Complexes for Biphasic Catalysis: An “ Extract ” Science” Prashant U. Naik and Robert D. Singer , 236th ACS National Meeting & Exposition, Philadelphia, PA, USA (08/08).

“Chelating ionic liquids for use in metal extractions and catalysis”, Robert D. Singer , Cytec Industries, Stamford, Connecticutt, U.S.A. (06/08) Invited .

“Chelating Task Specific Ionic Liquids”, Prashant U. Naik and Robert D. Singer, 91st Canadian Chemistry Conference (05/08)

“Ionic Liquids for Biodegradation and Organocuprate Chemistry” Jeff Farrell and R. D. Singer, 33rd Atlantic CIC Student Conference 2008, Halifax, N.S. (05/08).

“Synthesis of Metal Chelate Complexes Using a Task-Specific Ionic Liquid” Carrie-Lee A. Trider and Robert D. Singer, 33rd Atlantic CIC Student Conference 2008, Halifax, N.S. (05/08).

“The Investigation of 1-hexyl-3-methylimidazolium tributylstannate” Amy Holland and Robert Singer, 33rd Atlantic CIC Student Conference 2008, Halifax, N.S. (05/08).

“ICP-MS Analysis of Chlorine in Water-Immiscible Ionic Liquids” Amy Holland and Robert Singer, 33rd Atlantic CIC Student Conference 2008, Halifax, N.S. (05/08).

“Formation of Nanosize Aggregates in the Binary Mixture of an Ionic Liquid and an Anionic Surfactant” Jason G. Quinn, Kulbir Singh, Gerrard Marangoni, and Robert D. Singer, 33rd Atlantic CIC Student Conference 2008, Halifax, N.S. (05/08).

“Reactions of Organocuprates in Phosphonium-Based Ionic Liquids” Christian B. Kyle, Jeff Farrell, and Robert D. Singer, 33rd Atlantic CIC Student Conference 2008, Halifax, N.S. (05/08). Awarded Runner-up Graduate Poster.

“Synthesis of Metal Chelate Complexes Using a Task-Specific Ionic Liquid” Carrie-Lee A. Trider † and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/08)

“Design and Synthesis of Biodegradable Ionic Liquids for Organocuprate Chemistry” Jeff Farrell , M. Teresa Garcia, Peter J. Scammells, and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/08)

“Reactions of Organocuprates in Phosphonium-Based Ionic Liquids” Christian B. Kyle , Jeff Farrell, and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/08)

“Micelle formation of dialkylimidazolium based ionic liquids in water” Jason Quinn , Kulbir Singh, Gerrard Marangoni, and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/08)

“Chelating Task Specific Ionic Liquids” Prashant U. Naik and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/08)

“Chelating Task Specific Ionic Liquids” Ted Abraham , Prashant Naik, and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/08)

“Investigating a New Ionic Liquid: 1-hexyl-3-methylimidazolium tributylstannate” Amy Holland and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/08)

“Ionic Liquids – From Academic Curiosities to Viable Alternative Solvents and Extractants Robert D. Singer , University of Iowa (09/07) Invited

“Metal Chelates From a Task Specific Ionic Liquid” Robert D. Singer 90th Canadian Chemical Conference, Winnipeg, Manitoba (05/07) Invited

“Synthesis and Characterization of a New Ionic Liquid: 1-Hexyl-3-methylimidazolium tributylstannate” Amy Holland and Robert D. Singer, Atlantic CIC Student Conference 2007, Wolfville, N.S. (05/07).

“Biodegradable Ionic Liquids and their Use as Solvents for Diels-Alder Reactions” Darrell C. Dean and Robert D. Singer, Atlantic CIC Student Conference 2007, Wolfville, N.S. (05/07). Awarded Communication Prize

“Potential Application and Synthesis of an Iron (II) Chelate Complex Using a Task-Specific Ionic Liquid” Carrie-Lee A. Trider † and Robert D. Singer, Atlantic CIC Student Conference 2007, Wolfville, N.S. (05/07).

Phosphonium-based Ionic Liquids as Solvents for Organocuprate Reactions Jeff Farrell † and Robert D. Singer, Atlantic CIC Student Conference 2007, Wolfville, N.S. (05/07).

Reactions of Organocuprates in Trihexyltetradecylphosphonium-Based Ionic Liquids Christian B. Kyle and Robert D. Singer, Atlantic CIC Student Conference 2007, Wolfville, N.S. (05/07).

“Ionic Liquids – From Academic Curiosities to Viable Alternative Solvents and Extractants” Robert D. Singer, VCP - Monash University, Melbourne, Australia (03/07) Invited

“Ionic Liquids – From Academic Curiosities to Viable Alternative Solvents and Extractants” Robert D. Singer, University of South Florida, Tampa, Florida (03/07) Invited

“Ionic Liquids – From Academic Curiosities to Viable Alternative Solvents and Extractants” Robert D. Singer, University of New Brunswick, Fredericton, New Brunswick (02/07) Invited

“Metal Chelate Formation Using a Task-Specific Ionic Liquid” Christian Kyle , Jitendra R. Harjani, Tomislav Frišcic, Leonard R. MacGillivray, and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/07).

“Synthesis of Biodegradable Ionic Liquids and Their potential as Alternative Solvents” Darrell Dean , Peter J. Scammells, and Robert D. Singer, Maritime Inorganic Discussion Weekend (03/07).

“Exploitation of ionic liquids' properties as solvents in organic and organometallic reactions.” Robert D. Singer ACS Pharmaceutical Round Table on Green Chemistry, McGill University, Montreal (11/06). Invited

“Ionic Liquids and Green Chemistry” Robert D. Singer , 10th Canadian Pollution Prevention Roundtable (06/06) Invited Speaker .

“Functionalization of imidazolium salts with amino diacetic acid groups.” Jinendra Harjani and Robert D. Singer 88th CSC Conference, Halifax, Nova Scotia (05/06)

“Quantification of halide residues in water immiscible ionic liquids using ICP-MS” Dexiang Li and Robert D. Singer, 88th CSC Conference, Halifax, Nova Scotia (05/06)

“1-[4-(Carboxy)benzyl]pyridinium hexafluorophosphate and 1-[4-(Carboxy)benzyl]-3-methylimidazolium hexafluorophosphate as Task Specific Ionic Liquids” Amy Holland, Jeff Farrell , and Robert D. Singer 88th CSC Conference, Halifax, Nova Scotia (05/06)

“Ionic Liquids as Solvents for the Preparation of Homoallylic Alcohols” Ted Abraham , Darrell Dean and Robert D. Singer, 88th CSC Conference, Halifax, Nova Scotia (05/06)

“Functionalization of imidazolium salts with amino diacetic acid groups.” Jinendra Harjani and Robert D. Singer, Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, (03/06)

“Ionic Liquids as Solvents for the Preparation of Homoallylic Alcohols” Carrie-Lee Trider, Daniel Whynot, Darrell Dean and Robert D. Singer, Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, (03/06).

“Chelating ionic liquids: imidazolium salts containing ethylamine diacetic acid moieties”, Jitenrda Harjani and Robert D. Singer, 230th ACS National Meeting, Atlanta, USA, (04/06).

“Ionic Liquids: An Overview and Potential as Solvents in Pharmaceutical Processes” Robert D. Singer, Pfizer Pharmaceutical Ltd., Groton Connecticut, USA (02/06) Invited Speaker .

“Ionic Liquids: An Overview and Potential as Solvents in Pharmaceutical Processes” Robert D. Singer, Deakin University, Australia (02/06) Invited Speaker.

“Silylstannation chemistry in ionic liquids.” Robert D. Singer , Pacifichem 2005, Honolulu, USA

"Silylstannation Chemistry in Ionic Liquids" Robert D. Singer, Steven Dickson, and Michael Strümpel, 88th CSC Conference, Saskatoon, Saskatchewan (05/05).

"Ionic Liquids as Solvent for the Preparation of Homoallylic Alcohols" D.Dean and R.D. Singer, Atlantic CIC Student Conference, Saint John's, Newfoundland (05/05).

"1-[4-(Carboxy)benzyl]pyridnium tetrafluoroborate as a Task Specific Ionic Liquid" Amy Holland, Whitfield Lewis, and Robert D. Singer, Atlantic CIC Student Conference, Saint John's, Newfoundland (05/05).

"Ionic Liquids as Solvents for the Preparation of Homoallylic Alcohols" Darrell Dean and Robert D. Singer, Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, (03/05)

"Quantification of halide residues in water immiscible ionic liquids using ICP-MS" Dexiang Li and Robert D. Singer, Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, (03/05)

"Lewis Acidic Ionic Liquids in Chemical Synthesis: Prospective and Applications", Jitendra R. Harjani and Robert D. Singer, Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, (03/05).

"Synthesis of Task Specific Ionic Liquids (TSILs)", Whitfield Lewis and Robert D. Singer, Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, (03/05)

"Design and synthesis of novel imidazolium ionic liquids Evaluation as selective adsorbents", Haiwen Zhang and Robert D. Singer, Maritime Inorganic Discussion Weekend, Sackville, New Brunswick, (03/05)

"Green Chemistry & Ionic Liquids in Synthesis", Robert D. Singer, Atlantic Provinces Counsel on the Sciences (APICS) Tour Speaker, 2005.

"Bismetallations of Unsaturated Substrates in Ionic Liquids” Robert D. Singer, 228th ACS National Meeting, Philadelphia, USA, (08/04). Invited

“Quantification of Chloride Ion Impurities in Ionic Liquids Using ICP-MS Analysis” Robert D. Singer, Kristy McCamley, Nicholas A. Warner, Marc M. Lamoureux, and Peter J. Scammells, ICAAS, Saint Mary's University. (08/04).

“Addition Reactions of Silylstannane Reagents to Unsaturated Substrates in Ionic Liquids” Robert D. Singer, 87th CSC Conference, London, Ontario (06/04).

“Exploitation of ionic liquids as solvents in organic and organometallic reactions” Robert D. Singer, Canada-US Joint Workshop on Inniovative Chemistry in Clean Media, Montreal, Quebec (05/04) Invited

“Silylstannations of a,ß-Unsaturated Carbonyl Compounds in Ionic Liquids” Steve Dickson, Ivan Hemeon, and Robert D. Singer, Atlantic CIC Student Conference, Halifax, Nova Scotia (05/04).

“Task Specific Ionic Liquids” Whitfield Lewis and Robert D. Singer, Atlantic CIC Student Conference, Halifax, Nova Scotia (05/04).

“Regioselective Addition of Silylstannanes to Termianl Alkynes Using a Recyclable Palladium(0) Catalyst in Ionic Liquids” Ivan Hemeon and Robert D. Singer, 86th CSC / IUPAC Conference, Ottawa (08/03).

“Preparation of Task Specific Ionic Liquids” Gavin Beck and Robert D. Singer, 86th CSC / IUPAC Conference, Ottawa (08/03).

“Silylstannation of a,ß-unsaturated carbonyl compouinds in Ionic Liquids” Steven Dickson and Robert D. Singer, 86th CSC / IUPAC Conference, Ottawa (08/03).

“Recyclable Palladium(0)-Catalyzed Addition of Silylstannanes to Terminal Alkynes in Ionic Liquids”, Ivan Hemeon and Robert D. Singer, Atlantic CIC Student Conference, Sydney, Nova Scotia (05/03). Awarded 1st Prize Graduate Oral Presentation

“Synthesis of Novel Ionic Liquids as Potential Functional Ionic Liquids”, Gavin Beck and Robert D. Singer, Atlantic CIC Student Conference, Sydney, Nova Scotia (05/03).

“Regioselective Addition of Silylstannanes to a,ß-Unsaturated Carbonyl Compounds in Ionic Liquids”, Steve Dickson and Robert D. Singer, Atlantic CIC Student Conference, Sydney, Nova Scotia (05/03).

“Design, Synthesis, Characterization and Use of Ionic Liquids”, Robert D. Singer, E. Turner, C. Pye, I. Hemeon, J. Finden, 85th CSC Conference, Vancouver (06/02).

“Addition of Silylstannanes to Terminal Alkynes in Ionic Liquids”, I. Hemeon and R. D. Singer, poster at 85th CSC Conference, Vancouver (06/02).

“Ionic Liquids: Environmentally-friendly Solvents” Robert D. Singer, Environmental Chemistry Symposium preceding Atlantic CIC Student Conference, Cornerbrook, Newfoundland (05/02) - Invited.

“Synthesis, Characterization and an Ab Initio Investigation of 1-Alkyl-3-methylimidazolium Halides”, E. Turner, C. Pye, and R. D. Singer, Atlantic CIC Student Conference, Cornerbrook, Newfoundland (05/02) – Awarded 1st Prize Physical Chemistry Oral Presentation.

“Addition of Silylstannanes to Terminal Alkynes in Ionic Liquids”, I. Hemeon and R. D. Singer, Atlantic CIC Student Conference, Cornerbrook, Newfoundland (05/02) – Awarded 1st Prize Graduate Oral Presentation.

“MnO2 Oxidations of Allylic Alcohols in Ionic Liquids” Steve Dickson and Robert D. Singer, Atlantic CIC Student Conference, Cornerbrook, Newfoundland (05/02).

“Ionic Liquids: Green Solvents for Today and Tomorrow”, Robert D. Singer, Mount Allison University, Sackville, New Brunswick, 11/00 - Invited.

“The Use of an Ionic Liquid in the Synthesis of the Potential A1 Adenosine Receptor Agonist N6-(endo/exo-5,6-[N-(p-Toluenesulfonyl)imino]norborn-2-yl)adenosine”, Ivan Hemeon, Peter J. Scammells, and Robert D. Singer, poster at 84th CSC Conference, Montreal (05/01).

“MnO2 Oxidations of Allylic Alcohols and Ethers Using Ionic Liquids”, I. Hemeon, T. Lantz, R.D. Singer, poster presentation at 84th CSC Conference, Montreal (05/01).

“MnO2 Oxidations of Allylic Alcohols and Ethers Using Ionic Liquids”, I. Hemeon, T. Lantz, R.D. Singer, poster presentation at Atlantic CIC Student Conference, Dalhousie (05/01).

“The Use of Ionic Liquids In Diels-Alder Reactions of Furan”, C. DeAmicis, I. Hemeon, R. D. Singer, poster presentation at 84th CSC Conference, Montreal (05/01).

“The Use of Ionic Liquids In Diels-Alder Reactions of Furan”, C. De Amicis, I. Hemeon, R. D. Singer, poster presentation at Atlantic CIC Student Conference, Dalhousie (05/01).

“Synthesis and Characterization of Novel Ionic Liquids”, A. Lantz, J. Finden, G. Beck, R. Singer, poster presentation at 84th CSC Conference, Montreal (05/01).

“Synthesis and Characterization of Novel Ionic Liquids”, A. Lantz, J. Finden, G. Beck, R. Singer, poster presentation at Atlantic CIC Student Conference, Dalhousie (05/01). (Awarded second prize for Organic Chemistry) (05/01).

“Exploring the Correlation Between the Coulombic Interactions and Enthalpic Properties of Dialkylimidazolium Halides, E. Turner, Corey Pye, and Robert Singer, poster presentation at: 84th CSC Conference, Montreal (05/01).

“Exploring the Correlation Between the Coulombic Interactions and Enthalpic Properties of Dialkylimidazolium Halides, E. Turner, Corey Pye, and Robert Singer poster presentation at Atlantic CIC Student Conference, Dalhousie (05/01).

“Selected Applications of Ionic Liquids in Synthesis” Robert D. Singer, presented at the 220th ACS National Meeting, Washington, D.C., U.S.A. 08/00 - Invited.

"Diversity of Ionic Liquids in Synthesis” Robert D. Singer, presented at the 83rd Canadian Chemical Conference, Calgary, Alberta, 05/00 - Invited.

“Ambient Temperature Ionic Liquids as Reaction Media” Robert D. Singer, presented at the 11th RACI (Royal Australian Chemical Institute) Convention, Canberra, Australia, 02/00.

“The Use of an Ionic Liquid in the Synthesis of the Potential A1 Adenosine Receptor Agonist N6-(5,6-[N-(p-toluenesulfonyl)imino]norborn-2-yl)adenosine” Presented by Ivan Hemeon (Honours student) at 2000 Atlantic C.I.C. Student Conference, 05/00. Awarded 1st Prize Oral Presentation in Medicinal and Biological Chemistry Division.

“Synthesis of Three New Ionic Liquids” Presented by Gavin Beck (Undergraduate research Assistant) at 2000 Atlantic C.I.C. Student Conference, 05/00.

“Salty Solvents – Ionic Liquids as Reaction Media” Robert D. Singer, presented at the 82nd Canadian Chemical Conference, Toronto, Ontario, 06/99 - Invited.

“Dialkylimidazolium Haloaluminate Ionic Liquids as Reaction Media for Lewis Acid Catalyzed Ether Cleavage Reactions” Robert D. Singer, presented at the 81st Canadian Chemical Conference, Whistler, British Columbia, 06/98.

"Those Silyl Zincates and Salty Solvents" Robert D. Singer, presented at Young Organic Chemists' Workshop, Whistler, British Columbia, 06/98.0.

“The Cleavage of Ethers in 1-Alkyl-3-Methylimidazolium Haloaluminate Ionic Liquids” Presented by Laine Green (Undergraduate Research Assistant) at 1998 Atlantic C.I.C. Student Conference, 05/98.

“Ionic Liquids as Reaction Media for the Friedel-Crafts Acylation of Metallocenes” Robert D. Singer, presented at the 80th Canadian Chemical Conference, Windsor, Ontario, 06/97.

“1-Ethyl-3-methyloimidazolium Halogenoaluminate Melts as Reaction Media” Presented by Laine Green (Undergraduate Research Assistant) at the 80th Canadian Chemical Conference, Windsor, Ontario, 06/97. Awarded Best Inorganic Poster Presentation.

“A Low Temperature 29Si and 13C NMR Spectroscopic Study of Reaction Intermediates for the Conjugate Addition of PhMe2SiLi using Substoichiometric Amounts of Me2Zn.” Presented by Bonnie MacLean (Undergraduate Research Assistant) at 1997 Atlantic C.I.C. Student Conference, 05/97. Awarded First Prize Undergraduate Poster Presentation.

“Recent Developments in the use of 1-Ethyl-3-methylimidazolium Halogenoaluminate Melts as Reaction Media for the Friedel-Crafts Acylation of Ferrocene” Presented by Laine Green (Undergraduate Research Assistant) at 1997 Atlantic C.I.C. Student Conference, 05/97.

“The Effects of Dimethylzinc on the 1,4-Conjugate Addition of PhMe2-Unsaturated Carbonyl Compounds”,SiLi to a,ß Presented by Kim Hennigar (Undergraduate Research Assistant) at 1997 Atlantic C.I.C. Student Conference, 05/97.

"Recent Progress in the Addition of Trialkylzincate Reagents to a,ß-Unsaturated Substrates" Robert D. Singer, presented at the 79th Canadian Chemical Conference, St. John's, Newfoundland, 06/96.

"The Catalytic Effects of Dimethylzinc on the 1,4-Conjugate Addition of Dimethylphenylsilyllithium to a,ß-Unsaturated Carbonyl Compounds", Presented by Bonnie MacLean (Undergraduate Research Assistant) at the 79th Canadian Chemical Conference, St. John's, Newfoundland, 06/96.

"Molten Salts: Their Use as Reaction Media in the Acylation of Organometallic Compounds", Presented by Jacqueline Surette (Undergraduate Research Assistant) at 1996 Atlantic C.I.C. Student Conference, 05/96. Awarded Best Organic Oral Presentation.

"The Catalytic Effects of Dimethylzinc on 1,4-Conjugate Addition", Presented by Bonnie MacLean (Undergraduate Research Assistant) at 1996 Atlantic C.I.C. Student Conference, 05/96. Awarded Best Inorganic/Analytical Oral Presentation.

"Preparation of (E4, E10)-Dodecadienylacetate", Presented by Laine Green (Undergraduate Research Assistant) at 1996 Atlantic C.I.C. Student Conference, 05/96.

"Conjugate Additions of Zinc Halide Derived Trialkylsilyl(dialkyl)zincate Reagents" Robert D. Singer, presented at the 78th Canadian Chemical Conference, Guelph, Ontario, 05/95.

"A Methodological and Spectroscopic Study of Triorganozincate Reagents", Presented by Andrew Vaughan (Honours student) at 1995 Atlantic C.I.C. Student Conference, 05/95.

"X-ray Crystal Structure of 1,4-Diphenylbutadiyne", Presented by Jacqueline Surette (summer undergraduate research assistant) at 1995 Atlantic C.I.C. Student Conference, 05/95.

"Recent Advances in Conjugate 1,4-Additionsof Organometallic Reagents to Unsaturated Substrates" Robert D. Singer, Invited seminar, Acadia University, Wolfville, Nova Scotia, 03/95.

"Spectroscopic and Chemical Investigations of Cyanocuprate Reagents" Robert D. Singer, Invited seminar, Mount Allison University, Sackville, New Brunswick, 02/94.

"Spectroscopic and Chemical Investigations of Cyanocuprate Reagents" Robert D. Singer, Invited seminar, Dalhousie University, Halifax, Nova Scotia, 03/94.

"Effect of Coordinating Solvent on Higher Order Organocyanocuprates" Robert D. Singer, presented at the 75th Canadian Chemical Conference, Edmonton, Alberta, 1992.

"Additions of CuCN Derived Stannylcuprates to Terminal Alkynes: A Comparative Spectroscopic and Chemical Study" Robert D. Singer, presented at the 74th Canadian Chemical Conference, Hamilton, Ontario, 1991.

"Developments of New Rationally Designed Organocuprates" Robert D. Singer, presented at the 73rd Canadian Chemical Conference, Halifax, Nova Scotia, 1990.

"1,4-Additions of Chiral Mixed Trialkylsilylcuprates" Robert D. Singer, presented at the 73rd Canadian Chemical Conference, Halifax, Nova Scotia, 1990.

“Stannylboronation of a,ß-Enones.” Robert D. Singer, presented at the 72nd Canadian Chemical Conference, Victoria, British Columbia, 1989.

“The Formation of 3,7-Bis(Arylazo)-1,3,5,7-Tetraazabicyclo-[3.3.1]-Nonanes from the Reaction of Diazonium Ions with Ammonia Formaldehyde Mixtures" Robert D. Singer, presented at the 69th Canadian Chemical Conference, Saskatoon, Saskatchewan, 1986.

This page last modified Monday, 09-Jan-2012 13:33:32 AST