E. Eugene Gooch,  Professor of Chemistry                                         Last update:  7 February, 2008
(336) 278-6221 . . .Office: McMichael 311              E-mail: gooch@elon.edu

Specialty:  Chemical Education and Organic Chemistry

                                    (NMR, Natural Products, Organic Synthesis, Molecular Modeling)

 

Research and Scholarship:

Dr. Gooch is collaborating with Dr. Joel Karty (Elon) and Dr. Stephen Craig (Duke Univ.) on an undergraduate organic chemistry text to be published by Prentice-Hall in 2009.  In addition to this and the development of new undergraduate labs in organic chemistry, Dr. Gooch supervises research with undergraduate students in the areas described below. 

[Note:  Funding is not available for postdoctoral researchers.]


Natural products are organic substances have been isolated from plant and animal sources.  Many thousands of substances have been isolated over the centuries.  Many of them possess biological activity, leading to their application in medicines.  Notable examples are salicylic acid (from the willow tree, left) and taxol (from the pacific yew, right).  Research projects in this area involve the collection of selected plant material, extraction with suitable solvents and testing these extracts for biological activity.  Promising leads are pursued by isolating individual compounds and determining their structure by magnetic resonance (NMR) and mass spectrometry (MS).


There is substantial interest in Green Chemistry:  reducing adverse environmental impacts of chemical technology.  One means to accomplish this goal is the development of synthetic methods which avoid the use of organic solvents.  udentsDr. Gooch's students are investigating the use of microwaves to accelerate selected organic reactions. A number of researchers have found that organic reactions which normally run at 100-150oC for 2-4 hours can be performed in < 15 minutes in a microwave oven.  Both conventional domestic ovens and special reactors have been used to accelerate these reactions.  Appropriate solvents for microwave chemistry (DMF, alcohols, etc.) must have the ability to absorb microwave radiation.  However, in the ideal procedure, solvents are not even used; organic reactants are adsorbed onto samples of montmorillonite clay and irradiated with microwaves; afterwards the products are extracted with a minimum amount of solvent and purified.  

Applications of this research include the rational design and synthesis of potential anticancer agents.  Compounds such as the substituted styryl benzazole shown here (X = NH or O or S) are typical synthetic targets. Several research groups believe the most potent anticancer agents have molecular weights of 400 or less. 

A joint project with Dr. Linda Niedziela in the biology department (started fall, 2000) investigates the synthesis and toxicity testing of substituted 2-arylbenzimidazoles:   

 


 

Dr. Gooch collaborates with Dr. Eugene Grimley in the isolation and identification of flavonoids from honey.  The objective of this research is to identify specific substances which are unique to selected varieties (poplar, sourwood, etc.) of honey.


Finally, research involving the molecular modeling of small peptides can establish correlations between structure and fragmentation patterns observed in mass spectrometry. While most smaller molecules form fragments upon ionization, larger molecules absorb the energy of ionization more easily, and then undergo ordinary rearrangements in the gas phase.  The study of tetraglycines (gly4), hexaglycines (gly6), tetraalanines (ala 4) and hexaalanines (ala6) has shown an interesting pattern.  As the figure shows, these molecules tend to fold up on themselves in the gas phase. The dominant attractive force is hydrogen bonding between the terminal nitrogen (blue, lower right) with the nearby oxygen atoms (red, center and bottom center).  This work, now using more modern software, is being extended to octapeptides.
 

Selected Publications, Grants & Presentations

Biography:

A native of east Tennessee, Dr. Gooch received his B.S. in chemistry from Carson-Newman College (1973) and his Ph.D. from the University of Tennessee (1981) working with Professor George W. Kabalka (dissertation, "The Synthesis of Alkyl Iodides via Organoboranes"). His postdoctoral work included synthesis of radiopharmaceuticals using iodine-125 and carbon-11 (Dr. J. S.  Fowler, Brookhaven National Labs, 1981-2), and the synthesis of cyclopropyl amino acids (Dr. C. H. Stammer, University of Georgia, 1982-3).  He joined Elon in 1988 after five years at Union University, Jackson, TN.  He is a member of the American Chemical Society and Sigma Xi.