Subsection Officers for 2007

Chair,   Sorin Diaconesai, NJ State Toxicology Laboratory
Chair-elect,   Dr. Ish  Kumar,  Dickinson University, Metropolitan Campus
Immediate Past-Chair,   Dr. Hanae Haouari, New Jersey City University

Secretary,
Treasurer, Dr. Kenneth Yamaguchi

Board of Directors
Dr. Mihaela Leonida
Dr. Robert Mentore
Dr. Kenneth Yamaguchi
Dr. Grace Borowitz
Dr. Irving Borowitz
Prof. Rudolph Jones
Mr. Sorin Diaconesc

THE USE OF ORGANOLITHIUM REAGENTS IN ORGANIC AND ORGANOMETALLIC SYNTHESIS. M. Falcon and S. Anderson, School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah NJ, 07430.

Organolithium compounds, such as methyl lithium, are prepared by the reaction of organic halides with lithium metal. The purpose behind making these reagents is to generate a nucleophilic alkyl group. In organic chemistry, this group can be employed in attacking the carbonyl group of aldehydes and ketones. In organometallic chemistry, this group can attack carbon monoxide ligands that are bound to transition metals. It was shown that treating tungsten hexacarbonyl with methyl lithium leads to the formation of tungsten acyl and di-acyl species. These products were further investigated as potential nucleophiles. All reactions were monitored by infrared spectroscopy.
 

THE USE OF TRANSITION METAL HYDROGEN-TRANSFER CATALYSTS IN ORGANIC SYNTHESIS. A. Toth and S. Anderson, School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah NJ, 07430.

Traditionally, the hydrogenation of unsaturated organic compounds, such as alkenes, is performed using molecular hydrogen in the presence of a transition metal catalyst. The reaction can also be performed using no external source of hydrogen, via hydrogen-transfer catalysts. These catalysts remove molecular hydrogen from one reagent, such as isopropanol or cyclohexene, and transfer it to the organic substrate. The end result of the transfer hydrogenation reaction was recorded with IR spectroscopy and products are analyzed via gas chromatography. Using this method, it was shown that ketones and alkenes were successfully reduced to secondary alcohols and alkenes, respectively.
 

THE USE OF OXICLEAN IN ORGANIC OXIDATION REACTIONS. Chedzhemova and S. Anderson, School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah NJ, 07430.

The conversion of primary alcohols to aldehydes to carboxylic acids via an oxidation is usually performed using reagents such as potassium permanganate and chromic acid.These reagents are hazardous, difficult to use and are not environmentally friendly. In this project, the use of the detergent Oxiclean, and well as its active component sodium percarbonate were investigated as potential oxidizing agents. These reagents are safe to use and are not harmful to the environment. Using oxyclean and sodium percarbonate, benzaldehyde was successfully oxidized to benzoic acid.
 

PEGYLATION VIA AMINOALKYLATION: DEVELOPMENT OF REACTION CONDITIONS USING PEG-ALDEHYDE WITH AMINO COMPOUNDS  Angela A. Aggrey and Arthur M. Felix. School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah NJ, 07430.

Previous work reported from our laboratory focused on the successful pegylation of salicylic acid and acetylsalicylic acid at their phenolic ­OH and ­COOH sites, respectively. A follow-up study investigating the pegylation of 5-aminosalicylic acid prompted us to develop general conditions for site specific pegylation of amino-compounds. We have successfully attached PEG-aldehyde, synthesized in our laboratory, to a model compound; aminoethanol.  It was determined that an acidic environment of approximately pH 5 in the presence of sodium cyanoborohydride (NaCNBH3) was needed for a successful site-specific pegylation of this compound. The reaction was monitored using a kinetic study for optimal reaction time. Structure confirmation was determined by infrared spectroscopy. Reaction conditions for the aminoalkylation as well as results from the kinetic study will be discussed.

DEVELOPMENT OF NOVEL REACTION CONDITIONS FOR THE SYNTHESIS OF PEG-ALDEHYDE Catherine P. Post and Arthur M. Felix. School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah NJ, 07430.

Pegylation of proteins, at either the amino terminus or at the _-amino position of specific lysine residues, have become important targets since the resulting products have been reported to have advantageous therapeutic properties. The use of PEG-active esters for conjugation has been reported to result in non-specific attachment to proteins. Recent reports on the use of PEG-aldehyde, for site-specific conjugation to proteins, have prompted us to develop an alternate synthesis of these aldehyde pegylating reagents.  To this end we developed a one-step synthesis of PEG-aldehyde from poly(ethylene)glycol using pyridinium chlorochromate, an oxidizing agent that is used routinely in organic chemistry for the conversion of primary alcohols to aldehydes. Reaction conditions were developed for the synthesis of PEG2000- and PEG6000-aldehyde. Structure confirmation was determined by infrared spectroscopy. Reaction conditions for the preparation of PEG-aldehyde as well as results from the kinetic study will be discussed.
 

FIBRINOGEN EXTRACTION STUDIES USING POLY(N-HEXYL METHACRYLATE). Ravneet Nagi and Robert Mentore, School of Theoretical & Applied Science, Ramapo College of New Jersey , Mahwah, NJ 07430.
 
Buffered fibrinogen solutions and varying concentrations of poly(n-hexyl methacrylate) in chloroform were combined and shaken vigorously in order to determine the efficiency of the polymer in extracting fibrinogen from the aqueous phase. Results indicate that molecular interactions between the polymer and the protein led to encapsulation of fibrinogen, altering the density of the protein and ultimately allowing it to be removed from the aqueous phase and transported into the organic phase. Ultraviolet-Visible absorbance spectroscopy and fluorescence spectroscopy were used to characterize the efficiency of the extraction process. FTIR spectroscopy was used to confirm the formation of complexes of fibrinogen and poly(n-hexyl methacrylate). Preliminary results indicate that the extraction process is dependent upon the concentration of the polymer.
 
 

SURFACE PACKING OF POLYMER MONOLAYERS AT THE AIR-WATER INTERFACE. Taofik Atolagbe and Robert Mentore, Department of Chemistry, Ramapo College Of New Jersey, Mahwah, 07430.
 
The surface pressure-area isotherms of poly(methyl methacrylate)(PMMA) and poly(ethyl methacrylate)(PEMA) were measured at 23 ± 1 °C. Limiting areas were compared to determine surface arrangement of polymer chains. Results indicate that the polymer repeat units are not significantly different despite the extra methylene group in the side chain of PEMA: the limiting areas of PMMA and PEMA were 4.6 _1016 ± 1.4 _ 1016 nm2 and 4.31 _ 1016 ± 1.7_1016 nm2 respectively. These results will be compared to theoretical results from computer simulations. Preliminary results indicate that the arrangement of the polymers studied at the air-water interface involves an irregular sequence of loops, trains, and tails rather than a linear arrangement where all segments exist along the polymer backbone in the plane of the surface.
 

First part of the talk would involve application of biocatalysis in the preparation of enantiomerically pure pharmaceuticals, their intermediates, and fine chemicals by following approaches such as microbial screening, enzyme screening, and substrate-structure screening. The effect of substrate structure on chemo - and enantioselectivity of enzymes will also be discussed. Second part of the talk involves the specificity of penicillin-binding proteins (PBPs) with the ultimate goal to develop better antibiotics to overcome the problem of antibiotic resistance by bacteria. Natural peptidomimetic side chain specificity on the inhibition of PBPs by _-lactams was also studied. No evidence of specificity toward these side chains was found. Substrate recognition by these important enzymes is not yet understood.
 
Dr. Kumar holds a Ph.D. in bioorganic chemistry from the Institute of Microbial Technology, Council for Science Industrial Research Laboratory (Chandigarh, India). He did postdoctoral research work at the State University of New York, Upstate Medical University, Department of Biochemistry and Molecular Biology and at Wesleyan University, Department of Chemistry. At the present he is Assistant Professor of Pharmaceutical Chemistry at Fairleigh Dickinson University (Metropolitan Campus).
 

The chemistry programs of the following colleges are members of the Hudson-Bergen Chemical Society

Essex County College
Fairleigh Dickinson University
New Jersey City University
Ramapo College of New Jersey
St. Peter’s College
Stevens Institute of Technology

This is a forum for undergraduate students and their faculty mentors from colleges and universities that participate in the subsection’s activities to present the results of their research.   Outstanding graduating students are also being recognized (they receive the Hudson-Bergen Chemical Society Award consisting of a certificate and a book, courtesy of John Wiley and Sons). All the presenters will receive certificates and a book, courtesy of McGraw-Hill.

Students who wish to present posters must send an abstract via e-mail to mleonida@fdu.edu by April 2, 2007. The abstract should be in MS Word format and must include the names and addresses of the student(s) and their faculty adviser(s) in addition to the title of the abstract. The abstract should not exceed 200 words. The name of the student presenting the poster should be underlined. There is no registration fee.
 

Abstract:  Mr. Diaconescu will talk about forensic toxicology, his experience with the NJ State Toxicology Laboratory, and present some case studies.  Forensic toxicology is the application of the study of adverse effects of chemicals on living organisms to medical-legal investigation.
Mr. Diaconescu obtained his M.S. in Forensic Science (Forensic Toxicology track) in 2005 from John Jay College of Criminal Justice in New York.  He is a Forensic Analyst with the NJ State Toxicology Laboratory in Newark, NJ, and adjunct faculty with the School of Natural Sciences at Fairleigh Dickinson University in Teaneck, NJ.  He is a member of the Society of Forensic Toxicologists, and 2007 chair-elect of the Hudson-Bergen Chemical Society.