Home
Registration Information
Accomodations
Symposium Speakers
Former SFN Graduate Students and Post-Docs
Contact Organizers
Humor
Pictures
Plenary Lecture
Abstract 
Stephen F. Nelsen
65th Birthday Symposium
Madison, Wisconsin
June 3-4, 2005
Dennis H. Evans
Department of Chemistry,
The Multifaceted Electrochemistry of Nitro Compounds
In nonaqueous solvents, the initial step in the reduction
of nitro compounds is the one-electron reduction to form the anion radical.
The electron-transfer reaction itself is of considerable interest to
electrochemists because, at least in the case of aliphatic compounds, the
reaction is relatively slow causing significant overpotentials.
This is unusual for a simple electron-transfer reaction.
The anion radical can undergo various reactions, most notably cleavage
of the C-N bond to form nitrite and the corresponding alkyl radical.
The rate of this cleavage reaction is highly dependent on structure, a
subject that has been thoroughly explored.
In the case of para substituted a-nitrocumenes,
transition from homolytic to heterolytic cleavage was observed upon changing
the substituent. In a number of
dinitrocompounds C-N bond cleavage is of negligible importance on the
electrochemical time scale but for several, including trans-2,3-dinitro-2-butene,
9,10-dinitroanthracene and 3,6-dinitrodurene, two electrons are added at
almost the same potential. The
factors responsible for this behavior will be discussed.
Finally, for trans-a-nitrostilbene
a redox-catalyzed isomerization to the cis
isomer was observed during voltammetry or electrolysis.
The mechanism of this unusual reaction will be presented.
Biographical Sketch
EDUCATION:
BS Degree
-
MS Degree -
PhD Degree -
PRESENT
POSITION:
Professor of Chemistry,
UNIVERSITY
APPOINTMENTS:
California
Institute of Technology, Visiting Professor of Chemistry, January-March, 1990.
HONORS:
BS in
Chemistry with Honors,
Woodrow Wilson Fellow, 1960-1961 (Honorary)
Danforth Graduate Fellow, 1960-1964 (Honorary)
NIH Predoctoral Fellow, 1961-1964
C. N. Reilley Award, Society for Electroanalytical Chemistry, 1993.
University
Named Fellow of the Electrochemical Society, 1998
Manuel M. Baizer Award of the Division of Organic and Biological
Electrochemistry, Electrochemical Society, 2004
Member, Award Committee, Division of Analytical Chemistry Award in
Electrochemistry, 1987-1988.
Member, Committee on Professional Training, 1989-98.
International Society of Electrochemistry:
Co-chair, Division IV, Organic and Biological Electrochemistry,
1985-1987, 1991-1993. 1997-2000. National Secretary, USA, 1992-8.
Electrochemical Society: Organic
and Biological Electrochemistry Division:
Secretary-Treasurer, 1983-1985; Vice Chair, 1985-1987; Chair,
1987-1989.
Member, Linford Award Subcommittee, 1985-1988.
Chair, 2002-2006;
Chair, David C. Grahame Award Committee, 1987-1989; 1994-6, 2001.
Chair, ad hoc Committee to
Review the Division of Organic and Biological Electrochemistry, 1991-1992.
Member, Honors and Awards Committee, 2001-
OTHER
PROFESSIONAL
ACTIVITIES:
National Science Foundation, Chemistry Division Advisory Committee,
1978-1981
Air Force Office of
Scientific Research, Chemistry Research Evaluation Panel, 1982-1986
Member, Advisory Board, Analytical
Chemistry, 1983-1985
Vice-Chairman (1985) and Chairman (1986) of Gordon Research Conference on
Electrochemistry
Member, External Review Committee, Department of Chemistry,
Member, Metallobiochemistry Study Section, National Institutes of Health,
1988.
Member,
Visiting Committee of the Department of Chemistry, Lehigh University,
1989-1993; 1996-
Member, Editorial Board, Journal of
Electroanalytical Chemistry, 1989- .
Member, External Review Committee, Department of Chemistry,
Member, Chemistry Evaluation Panel, National Science Foundation Graduate
Fellowship Program, National Research Council, 1991, 1992, 1993.
Member, External Review Committee, Department of Chemistry,
Member, Editorial Advisory Board, Critical
Reviews in Analytical Chemistry, 1992- .
Member, Editorial Advisory Board, Inorganic
Chemistry, 1993-1995.
External Referee for Faculty Appointments, Department of Chemistry,
Quaid-I-Azam University, Islamabad, Pakistan, 1995-
Member, National Visiting Committee, Workshop
Chemistry Project,
Associate
Editor, Journal of the Electrochemical Society, July 2000-
Recent Publications (from a total of 182)
168.
"Synthesis and Characterization of Bifunctional Molecules Intended
for Studies of Intramolecular Electron Transfer", Z.-R. Zheng and D. H.
Evans in A. J. Fry and Y. Matsumara, Eds., New Directions in Organic
Electrochemistry, Electrochemical Society, Pennington, NJ, 2000, pp 88-91.
169.
"Anomalous Behavior in the Two-Step Reduction of Quinones in
Acetonitrile", M. W. Lehmann and D. H. Evans, J.
Electroanal. Chem. 2001, 500, 12-20..
170.
“Voltammetric Study of an Unusual Dimer/Monomer Redox System
Involving a Chromium(III) Complex of a Tridentate CNN Ligand”, S.
Leelasubcharoen, M. W. Lehmann, K. H. Theopold and D. H. Evans, J.
Electrochem. Soc. 2001, 148, E118-E120.
171.
“Mechanism of the Electrochemical Reduction of 3,5-Di-tert-butyl-1,2-benzoquinone.
Evidence for a Concerted Electron and Proton Transfer Reaction
Involving a Hydrogen-Bonded Complex as Reactant”, M. W. Lehmann and D. H.
Evans, J. Phys. Chem. B 2001, 105, 8877-8884.
172.
“One-Step Synthesis of Substituted
6-Amino-5-cyanospiro-4-(piperidine-4')-2H4H-dihydropyrazolo[3,4-b]pyrans”,
A. M. Shestopalov, Y. M. Emeliyanova, A. A. Shestopalov, L. A. Rodinovskaya,
Z. I Niazimbetova and D. H. Evans, Org. Lett. 2002, 4,
423-425.
173.
“Synthesis and Electrochemical Investigation of
Oligo-(arylenevinylenes) Intended for the Preparation of Two-dimensional
Polymer Networks”, Z. I. Niazimbetova, A. Menon, M. E. Galvin and D. H.
Evans, J. Electroanal. Chem. 2002, 529, 43-50.
174.
“Voltammetric Studies of the Reduction of cis- and trans-a-Nitrostilbene”,
D. H. Evans, C. Kraiya and Z. V. Todres, in M. S. Workentin, F. Maran and
K. Chiba, Eds., Organic Electrochemistry.
Proceedings of the Fifth International Manuel M. Baizer Symposium in
Honor of Professor Jean Michel Savéant, Electrochemical Society,
Pennington, NJ. 2002, 108-111.
175.
“Voltammetric Studies of Rhenium(V) Compounds Containing the
2-(2’-Hydroxyphenyl)-2-oxazoline Ligand”, C. C. Van Kirk, V. Béreau, M.
M. Abu-Omar and D. H. Evans, J. Electroanal. Chem. 2003, 541,
31-38.
176.
“Potential Inversion in the Reduction of trans-2,3-Dinitro-2-butene”,
M. W. Lehmann, P. Singh and D. H. Evans, J. Electroanal. Chem. 2003,
549, 137-143.
177.
“Bifunctional Molecules that Receive Two Electrons Sequentially and
Reversibly through Only One of their Two Reducible Groups”, Z.-R. Zheng and
D. H. Evans, J. Electroanal. Chem 2004,
558, 99-107.
178.
“Revisiting the Heterogeneous Electron-Transfer Kinetics of Nitro
Compounds”, C. Kraiya, P. Singh and Dennis H. Evans, submitted to J.
Electroanal. Chem. 2004, 563, 203-212.
179.
“Cross Condensation of Derivatives of Cyanoacetic Acid and Carbonyl
Compounds. Part 1.
Single-Stage Synthesis of Substituted
6-amino-spiro-4-(N-R-piperidine-4’)-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles”,
A. M. Shestopalov, Y. M. Emeliyanova, A. A. Shestopalov, L. A. Rodinovskaya,
Z. I. Niazimbetova and D. H. Evans, Tetrahedron
2003, 59, 7491-7496.
180. “Studies
of the Oxidation of a Hydroxychromium(III)-[hydrotrispyrazoylborate]pyarazolyl
Complex”, C. C. Van Kirk, K. Qin, K. H. Theopold and D. H. Evans, J.
Electroanal. Chem.
2004,
565, 185-190.
181. “Voltlammetric
Studies of the Reduction of cis- and trans-a-Nitrostilbene”, C. Kraiya, P. Singh, Z. V.
Todres and D. H. Evans, J.
Electroanal. Chem.
2004, 563, 171-180.
182.
“Investigation of Potential Inversion in the Reduction of
9,10-Dinitroanthracene and 3,6-Dinitrodurene”, C. Kraiya and D. H. Evans, J.
Electroanal. Chem. 2004, 565,
29-35.
Last Updated: January 10, 2005 (P.M. Gannett)