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Dr. Peter de Lijser

Professor Organic Chemistry
Department Chair

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Physical organic chemistry - mechanistic and kinetic studies of reactions involving radical and radical ion intermediates. Drug discovery - rational drug design and synthesis; structure/reactivity studies of drug candidates (in collaboration with Dr. Nilay Patel in Biological Science).

 

Office: MH-582G
Phone: (657) 278-3290
Lab: DBH-180
Phone: (657) 278-5274
Email:This email address is being protected from spambots. You need JavaScript enabled to view it.


Courses Taught

  • CHEM 115 Introduction to General Chemistry
  • CHEM 200 Chemistry for Nursing and Allied Health Professionals
  • CHEM 301A/B Organic Chemistry
  • CHEM 302 Organic Chemistry Laboratory
  • CHEM 313 A-C Environmental Pollution and Solutions
  • CHEM 431 Advanced Organic Chemistry
  • CHEM 505A/B Seminar
  • CHEM 537 Organic Spectroscopy

Education

Postdoctoral University of Rochester, Rochester, NY
Ph.D. Dalhousie University; Halifax Nova Scotia, Canada
M.Sc. Leiden University; Leiden, Netherlands
B.Sc. Van Leeuwenhoek Institute; Delft, Netherlands


Research Interests

Research in the de Lijser group is two-fold. We use physical organic techniques to study the reactive intermediates formed in the enzymatic and photooxidative processes of xenobiotic compounds used as drugs and pesticides (mostly those with oxime and oxime ether functionalities). The reactive intermediates are generated by thermal and photochemical techniques. Molecules of interest are synthesized, purified and characterized. The chemistry of the reactive intermediates is explored by laser flash photolysis and steady state photolysis experiments. Products are analyzed by gas chromatography, mass spectrometry and NMR techniques. We have shown that several different reactive intermediates are involved in the electron transfer reactions of oximes and oxime ethers. Current research interests are geared towards learning more about the specific reactivities of the different reactive intermediates, including iminoyl and iminoxyl radicals, in order to be able to exploit them in different processes.

In a collaborative project with Dr. Nilay Patel (Department of Biological Science, CSUF) we design and synthesize small organic molecules that can be used to maintain the pluripotency of stem cells. The goal of this collaboration is to design and synthesize drugs that can be used to block two proteins from interacting with one another and thereby promoting pluripotency in stem cells. The desired molecules are designed by molecular modeling and synthesized in the laboratory. A secondary goal is to perform a structure-reactivity study on a series of drugs in which only one small change occurs. We are currently focusing on several different classes of molecules (chalcones, amides, small peptides, carboxylic acids and esters), some of which have shown promising results in biological studies carried out by our collaborators in the Department of Biological Science at CSUF.


Selected Publications

"Highly Efficient Formation of Nitriles and Alkoxy Radicals From N-Alkoxyiminoyl Radicals in Solution", de Lijser, H.J.P.; Burke, C.R.; Rosenberg, J.; Hunter, J. J. Org. Chem., 2009, 74, 1679-1684.

"Mechanistic Aspects of the Formation of Aldehydes and Nitriles in Photosensitized Reactions of Aldoxime Ethers", de Lijser, H. J. P.; Rangel, N. A.‡; Tetalman, M.‡; Tsai, C. K. J. Org. Chem., 2007, 72, 4126-4134.

"Effect of Structure in Benzaldehyde Oximes on the Formation of Aldehydes and Nitriles Under Photoinduced Electron Transfer Conditions", de Lijser, H. J. P.; Hsu, S.‡; Marquez, B. V.‡; Park, A.‡; Sanguantrakun, N.; Sawyer, J. R.‡ J. Org. Chem., 2006, 71, 7785-7792.

"Quinone-Sensitized Steady-State Photolysis of Acetophenone Oximes Under Aerobic Conditions: Kinetics and Product Studies", Park, A.‡; Kosareff, N. M.‡; Kim, J. S.; de Lijser, H. J. P. Photochem. Photobiol., 2006, 82, 110-118.

"Photochemical Acetalization of Carbonyl Compounds in Protic Media Using an in Situ Generated Photocatalyst", de Lijser, H. J. P.; Rangel, N. A.‡ J. Org. Chem., 2004, 69, 8315-8322.

"Photosensitized Reactions of Oxime Ethers. A Steady-State and Laser Flash Photolysis Study", de Lijser, H. J. P.; Tsai, C. K. J. Org. Chem., 2004, 69, 3057-3067.

"Preparation and Structure of an Unexpected Dehydrogenation Product from 2,6-Diphenylcyclohexanone Oxime", de Lijser, H. J. P.; Dedeian, C. E.‡; Sawyer, J. R.‡; Herron, S. R.; Kantardjieff, K. A. J. Chem. Cryst., 2004, 34, 103-110.

"Substituent Effects in Oxime Radical Cations. 1. Photosensitized Reactions of Acetophenone Oximes", de Lijser, H. J. P.; Kim, J. S.; McGrorty, S. M.‡; Ulloa, E. M.‡ Can. J. Chem., 2003, 81, 575-585.

"Photosensitized Regeneration of Carbonyl Compounds From Oximes", de Lijser, H. J. P.; Fardoun, F. H.; Sawyer, J. R.‡; Quant, M.‡ Org. Lett., 2002, 4, 2325-2328.

(‡ = undergraduate co-author)