E. Eugene Gooch,
Professor of Chemistry Last update:
7 February, 2008
(336) 278-6221 . . .Office: McMichael 311
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.]
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
are salicylic acid (from the willow tree, left) and taxol
(from the pacific yew, right). Research projects in this area involve the
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
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
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
fall, 2000) investigates the synthesis and toxicity testing of substituted
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
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.
Grants & Presentations
in the Chemistry Curriculum: Outcomes and Benefits from the Teaching of
Medicinal Chemistry” ACS National Meeting, San Francisco, CA, 12 September,
2006, Division of Computers in Chemistry #184
Chemistry at Three Piedmont Colleges”, E. Gooch, A. Glenn (Guilford
College) and Erland Stevens (Davidson College) – 55th Southeast
Regional Meeting, CHED # 284
and Mechanisms: An Experiment with a Focused Recitation for Organic
Chemistry” E. Gooch and Joel Karty – 55th Southeast Regional
Meeting. CHED # 285
- “A Tale of
Two Courses: Medicinal Chemistry at Two Piedmont Colleges. E. E. Gooch, A.
G. Glenn (Guilford College) -- 225th ACS National Meeting, COMP #
- "Experiments for Organic Chemistry Lab I" (formerly McGraw-Hill,
ISBN 0-07-229537-6 now published independently Fall, 2001-3)
- "Experiments for Organic Chemistry Lab II" (published independently
- "Chemistry and Warfare--A Liberal Arts Course in Chemistry" -- (
Jour. Chem. Ed.
, (2002) 79, 820)
- Ruth, V. Brummer, W. Gooch, E. & Sienerth, K. "Micelle-modified
Colorimetric Method for the Determination of Aqueous Hg2+ and Zn2+" (Environmental
Testing and Analysis, accepted
- “Moving Past Markovnikov’s
Rule”, Jour. Chem. Educ.
(2001) 78, 1358..
of the Iodine Value of Selected Oils:
An Experiment Combining FTIR Spectroscopy with Iodometric
The Chemical Educator
(2001) 6, 7-9.
- "Experiments for CHM 472 -- Modern NMR Lab" (published independently
- "Evaluation and Refocusing Chemical Safety Practices and Instruction
at a Mid-Size College" Chap. 11 in
Educating for OSHA Savvy Chemists
(ACS Symposium Series 700), P.J.Utterback & D.A. Nelson,
Eds. (Amer. Chem. Soc., 1998)
NSF-ILI Grant # 96-50908
"Acquisition of a Fourier-Transform IR Spectrometer to Enhance Undergraduate
"Force Field Modeling of Protonated Tetraglycine: Correlation with Mass
Spectrometric Observations", E. E. Gooch and M. M. Bursey, Biol. Mass.
Spect. (1993) 143. (45th ACS SE Regional Meeting, Johnson City, TN,
10/17/93, Abstract # 222).
"Methyl Red: Two Colorful Acid-Base Extractions", E. E. Gooch,
Jour. College Sci. Teaching (1990)
"Synthesis of Iodohexane via Hydroboration-Iodination: A Microscale Organic
Laboratory Experiment Involving Air-Sensitive Compounds," E. E. Gooch,
J. Chem. Educ. (1990) 67, A232.
"The Reaction of Organoboranes with Olefinic oc,ß-Unsaturated Compounds,"
G. W. Kabalka, Y. Z. Gai, N. M. Goudagon, R. S. Varma & E. E. Gooch,
Organometallics, (1988) 7, 493.
"The Synthesis of Cholesterol Alkyl Ethers," E. E. Gooch & B. R. Ross,
J. Tenn. Acad. Sci. (1985) 112.
"A New Synthesis of Racemic Coronamic Acid and Other Cyclopropyl Amino
Acids," M. Suzuki, E. E. Gooch & C. H. Stammer, Tet. Lett. (1983)
"Rapid & Mild Synthesis of Radioiodine-Labeled Radiopharmaceuticals,"
G. W. Kabalka, E. E. Gooch & K. A. R. Sastry, J. Nuc. Med. (1981)
"New Method for Radioiodinating Organic Compounds via Organoborane Reactions,"
G. W. Kabalka & E. E. Gooch, Chem Comm. (1981) 1011.
"Di- and Trimethoxystyryl Derivatives of Heterocyclic Nitrogen Compounds,"
C. T. Bahner, L. Rives, E. E. Gooch,
Arzneimittel Forschung (1981)
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.