Saint Mary's

Chemistry
Professor
Phone: 902.496.8189
Office: Science S522
Email: robert.singer@smu.ca

Research Interests:
Organic Chemistry; New Methodologies in Synthesis; Catalysis in Ionic Liquids; Biomass Processing in Ionic Liquids; Ionic MOFs; Green Chemistry; Ionic Liquids as Reaction Media Related to Organometallic Methodology.

Biographical Sketch

B.Sc. (Saint Mary's)
Ph.D. (Simon Fraser)
Alexander von Humboldt Fellow (Universität Marburg, Germany)
Father William Stewart S.J. Medal for Excellence in Teaching, Saint Mary's, 1999
Honorary Associate, Victorian College of Pharmacy, Monash University, 2007-2010
Canadian Association of University Teachers Dedicated Service Award, 2012
Anderson Award for Excellence in Teaching and Research (Memorial University), 2020

Dr. Singer, born and raised in Nova Scotia, obtained his B.Sc. Honours (First Class) at Saint Mary's 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 in the Department of Chemistry at Saint Mary's. He has served two terms as Chair of the Department of Chemistry, two years as the Director of Engineering and has been a member of the University's Academic Senate and Board of Governors.

General

Since becoming a faculty member in the department of Chemistry at Saint Mary's Dr. Singer has employed over 150 undergraduate research assistants including 34 Honours students, 4 Masters students, a Doctoral student, and 14 post-doctoral fellows. He has attracted > $11 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, NS-MRDF, Research NS, and PRAC. His current research interests lie in the field of Green Chemistry with particular emphasis on Catalysis and Biomass Processing in Ionic Liquids. A recent area of interest lies in the area of ionic Metal Organic Frameworks (iMOFs) as functional materials. These areas of interest are 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).

The use of room temperature ionic liquids (RTILs) in chemical applications has gained significant and varied interest over the last few decades. In addition to use as novel reaction media they have enjoyed applications in materials, catalysis, and separations amongst others. RTILs possess a unique set of chemical and physical properties, some of which are tuneable, making them attractive targets for investigation. Such properties include tuneable liquid range and viscosity, volatility, polarity, and biodegradability. RTILs can also have high conductivity, thermal and electrochemical stability and superior solvating ability.

The overall theme of our research program involves the exploitation of the useful chemical and physical properties of RTILs while being mindful of applying Green Chemistry principles whenever possible. Consequently, our research program has evolved into four main areas of interest: (1) The development of novel ionic organocatalysts that can be recycled through their use in RTIL systems.; (2) The use of ligands based on ionic liquid cores in the synthesis of ionic Metal Organic Frameworks (iMOFs) (3) The design, synthesis, and characterization of new ionic liquids for use as alternative solvents and materials targeted toward biomass conversion.; (4) Adaptation of bimetallic and organometallic addition reactions to RTIL systems.; (5) The development of functionalized RTIL’s for use in metal separations or in the preparation of RTIL–metal complexes that can be easily recycled as immobilized homogeneous catalysts.

Links to Related Research

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 Previous Honours Students

• Jacob Campbell – M.Sc. (in progress), Dalhousie University
• Katherine Parsons – Ph.D. (in progress), Dalhousie University
• Daniel O’Hearn – Ph.D. (in progress), University of Limerick, Ireland
• Julia Killorn – Health Canada – Drug Analysis
• Kyle Awalt – Ph.D. (in progress), Monash University Institute for Pharmaceutical Sciences, Australia
• Andrew Watson – Medical School, University of Ottawa
• Trevor McGrath – M.D., University of Ottawa
• Chris Lavoie – Ph.D., Dalhousie University (PGS-M; PGS-D; Banting-PDF)
• Christine Prudhoe – M.D., University of Ottawa
• Kenson Ambrose - Ph.D., Memorial University
• Tyler Cuthbert – Ph.D., Western University
• Alanna Durand – M.D., University of Calgary
• Alwyn Gomez – M.D., Dalhousie University
• Jeanna MacLeod – M.Sc., Memorial University
• Ted Abraham – Ph.D., Monash University, Australia
• Stephanie Russell – Ph.D., University of Western Australia
• Jeff Farrell – Ph. D., University of Toronto, Toronto, Ontario; CGS-M
• Carrie-Lee Trider – M.D., Dalhousie University
• Amy Holland – M.Sc., Queen's University, Kingston, Ontario; NSERC-PGS-M
• Darrell Dean - Ph. D., Queen's University, Kingston, Ontario; NSERC-PGS-M
• Whitfield Lewis – M.D., American University of the Caribbean
• Steven Dickson - Ph. D., Queen's University, Kingston, Ontario
• Gavin Beck – M.D., Dalhousie University
• Elizabeth Turner - Ph.D., University of Western Ontario, NSERC PGS A and CGS-D scholarship winner
• Ivan Hemeon - Ph.D., Simon Fraser University, M.Sc. Applied Science, Saint Mary's, NSERC PGS A and CGS-D scholarship winner
• Jeremy Finden - Ph. D., Queen's University, Kingston, Ontario; NSERC PGS A scholarship winner
• Kim Hennigar - MBA, Saint Mary's
• Kevin Kells - Ph. D., 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 - D.V.M.,UPEI Veterinary School, 2001; 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.

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 Teaching 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

Publications (2010-2020 only):

Tom Steele, Robert D. Singer, Susan Bjornson “Effects of food availability on microsporidiosis and alkaloid production in the two spotted lady beetle, Adalia bipunctata L.” J. Invert. Path. 2020, 172, 107443 – 107446 doi.org/10.1016/j.jip.2020.107443

Tom Steele*, Susan Bjornson, Robert D. Singer “Effects of temperature on alkaloid production and microsporidiosis in the two-spotted lady beetle, Adalia bipunctata L. (Coleoptera: Coccinellidae) J. Invert. Path. 2020, 172, 107353 - 107359 doi.org/10.1016/j.jip.2020.107353

Jon Kyle Awalt, Peter J. Scammells, and Robert D. Singer* “Liquid assisted grinding (LAG) for the     N-demethylation of alkaloids” ACS Sustainable Chem. Eng. 2018 2018, 6, 10052-10057 DOI:10.1021/acssuschemeng.8b01393.

Daniel J. O’Hearn and Robert D. Singer* “Direct Synthesis of a Copper(II) N-heterocyclic Carbene Complex in Air” Organometallics 2017, 36 (17), 3175-3177 DOI:10.1021/acs.organomet.7b00489

Jon Kyle Awalt, Raymond Lam, Barrie Kellam, Bim Graham, Peter J. Scammells, and Robert D. Singer* “Utility of iron nanoparticles and a solution-phase iron species for the N-demethylation of alkaloids”  Green Chemistry 2017, 19, 2587 – 2594 DOI: 10.1039/C7GC00436B

Christian Díaz-Urrutia, Bitu B Hurisso, Patrick M Gauthier, Baburam Sedai, Robert D Singer, R. Baker* “Catalytic Aerobic Oxidation of Lignin-Derived Bio-Oils Using Oxovanadium and Copper Complex Catalysts and Ionic Liquids” J. Mol. Cat. A: Chem. 2016, 423, 414-422.

Trevor McGrath, Katherine N. Robertson, Jason D. Masuda, Jason A. C. Clyburne, and Robert D. Singer* “Ionic Thiourea Organocatalysis of the Morita-Baylis-Hillman Reaction” Aust. J. Chem. 2016, 69, 759-762.

Leigh Ford, Kai E. O. Ylijoki, Robert D. Singer, Peter J. Scammells “Nitrogen Containing Ionic Liquids: Biodegradation Studies and Utility in Base Mediated Reactions” Aust. J. Chem. 2015, 68, 849-857. 

Kenson Ambrose, Bitu B. Hurisso, and Robert D. Singer* “Recyclable Ionic Liquid Tagged Co(Salen) Catalysts for the Oxidation of Lignin Model Compounds” Can. J. Chem. 2013, 91: 1258-1261. dx.doi.org/10.1139/cjc-2013-0336.

Scott G. Harroun, Theodore J. Abraham, Christine Prudhoe, Yaoting Zhang, Peter J. Scammells, Christa L. Brosseau*, Cory C. Pye*, Robert D. Singer* “Electrochemical Surface-Enhanced Raman Spectroscopy (E-SERS) of Novel Biodegradable Ionic Liquids” Phys. Chem. Chem. Phys. 2013, 15, 19205-19212, DOI: 10.1039/c3cp52916a.

Swapnil Sonar, Kenson Ambrose, Arthur D. Hendsbee, Jason D. Masuda, and Robert D. Singer* Can. J. Chem. 2012, 90(1): 60-70  “Synthesis and application of Co(salen) complexes containing proximal imidazolium ionic liquid cores” Invited Contribution.

Leigh Ford, Farzad Atefi, Robert D. Singer and Peter J. Scammells* Eur. J. Org. Chem. 2011, 942-950.  “Grignard Reactions in Pyridinium and Phosphonium Ionic Liquids”

Leigh Ford, Jitendra R. Harjani, Farzad Atefi, M. Teresa Garcia, Robert D. Singer, and Peter J. Scammells Green Chemistry 2010, 1783 – 1789  DOI: 10.1039/C0GC00082E  “Further studies on the biodegradation of pyridinium ionic liquids”

Gaik B. Kok, Cory C. Pye, Robert D. Singer, and Peter J. Scammells*  J. Org. Chem. 2010, 75, 4806-4811“An Efficient Two-step Iron(0)-mediated N-Demethylation of N-Methyl Alkaloids”

Jitendra R. Harjani, Theodore J. Abraham, Alwyn T. Gomez, M. Teresa Garcia, Robert D. Singer,* and Peter J. Scammells* Green Chemistry 2010, 12, 650 - 655 ”Sonogashira Coupling Reactions in Biodegradable Ionic Liquids Derived from Nicotinic Acid”

Patents filed:

Robert D. Singer and John Steele “Antifouling Marine Paints” Provisional Patent filed in US Patent and Trademark Office (USPTO), March 20, 2014 application #: 61/968,305.

Robert D. Singer and Prashant Upendra Naik “Ionic liquids comprising ligands containing positively charged heterocyclic rings useful for metal extractions” U.S. Pat. Appl. Publ. (2010) US 20100324273 A1 20101223

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

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.

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.

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.

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

Book Chapters and Review Articles (Senior Author marked with asterisk):

I. Hemeon, A. Durand, and R. D. Singer*Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silylzinc Reagents, Volume 4, Chapter 4.4.9 Knowledge Update  2013, 141-149.

Naik, P. U., Trider, C.L., Farrell, J., Singer, R. D. “Ionic Liquid Complexes for Metal Extractions and Biphasic Catalysis” I & EC ACS Symposium Series, Ionic Liquids: From Knowledge to Application, Chapter 17, pp 239–253, Chapter DOI: 10.1021/bk-2009-1030.ch017, ACS Symposium Series, Vol. 1030 ISBN13: 9780841269972eISBN: 9780841224919 Publication Date (Web): December 18, 2009 Copyright © 2009 American Chemical Society

Peter J. Scammells, Janet L. Scott, Robert D. Singer Aust. J. Chem. 2005 58, 155-169 Review. “Ionic Liquids – The Neglected Issues” – Invited, Front Cover { # 4 on the “Most Read Since 2000” list in Aust. J. Chem.}

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

D. Singer*Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silyllithium Reagents, Volume 4, Chapter 4.4.11, 2002, pg. 237 - 246.

D. Singer*Houben-Weyl Methods of Molecular Transformations, Science of Synthesis Silylcopper Reagents, Volume 4, Chapter 4.4.10, 2002, pg. 231 - 236.

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 - 230.

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 - 224.

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 - 218.

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 - 210.

Paul Knochel* and Robert D. Singer, Chemical Reviews, 1993, 93, 2117 - 2187. “Preparation and Applications of Polyfunctional Organozinc Reagents in Organic Synthesis”