Christopher Hadad
Professor and Vice Chair for Research & Administration
187 CBEC Building
151 W Woodruff Ave
Columbus, OH 43210
Areas of Expertise
- Organic
Bio
Professor Hadad received his B.S. with Honors degree in Chemistry from the University of Delaware in 1987. He was a Fannie and John Hertz pre-doctoral fellow at Yale University and obtained his Ph.D. degree in Organic Chemistry with Professor Kenneth Wiberg in 1993. He was a National Science Foundation post-doctoral fellow (1992 — 1994) at the University of Colorado (Boulder) with Professor Charles DePuy, and he then joined the Ohio State University in 1994 as an assistant professor. He has been honored with a National Science Foundation CAREER award.
Research Overview
The central research focus of our team's efforts is on the study of reaction mechanisms. We are interested in a diverse set of circumstances for these investigations – from biochemical applications in which organic transformations occur in an enzyme's active site; (2) the reactions of reactive oxygen species in biochemical, atmospheric (environmental) and combustion environments; (3) the role of reactive intermediates in these reaction mechanisms, especially after photochemical generation; and (4) the optimization of homogeneous and heterogeneous catalysts for improved conversion of chemical feedstocks. Thus, our research interests lie in understanding the kinetics and thermodynamics of reactive intermediates in the gaseous and condensed phases, and as applied to important applications including chemical biology, environmental chemistry, and energy conversion. Towards these goals, we use a variety of experimental and computational methods to study these diverse problems. We use computational methods for the in silico design of novel drugs, inhibitors, or enzymes for improved efficacy – often with the tools of electronic structure theory, molecular docking, molecular dynamics, hybrid quantum mechanical/molecular mechanical (QM/MM) methods. We then verify our theoretical predictions with a variety of experimental methods, including organic synthesis, chemical kinetics, photoaffinity labeling, and mass spectrometry.
A variety of synergistic experimental and computational efforts are currently underway in the research group. A number of projects are targeting the design of novel enzymes for novel function or developing new routes for protection from exposure to organophosphorus (OP) agents, including pesticides and chemical nerve agents. Using tools of rapid in silico design, we are designing, and then verifying, the improved function of novel enzymes and chemical reactivators for protection against OPs. In addition, we are developing novel spin probes for the in vivo detection of biological agents using trityl radicals and electron paramagnetic resonance imaging. In energy applications, we are studying the reaction mechanisms for creating hydrogen fuel cells from various precursors. We are also interested in the conversion of value-added chemicals from biomass sources, in order to reduce our dependence on petroleum sources. In environmental applications, we are interested in the fate of organic pollutants in the environment, including the oxidation of polycyclic aromatic hydrocarbons under both biochemical, aqueous and atmospheric conditions.
Currently, our research is supported by the National Science Foundation, the National Institutes of Health, the Defense Threat Reduction Agency, and the US Army Medical Research Institute of Chemical Defense.
Previous members of the research group have taken on positions in industry and in academia. Recently, students have found employment at 3M, Chemical Abstracts, Dow Chemical, Marathon Oil, Procter & Gamble, Lubrizol and Vertex. Students interested in academic positions have taken assistant professor positions at diverse schools, including Bowdoin College, Indian Institute of Technology-Bombay, Iowa State University, Otterbein College, St. Louis University, Virginia Commonwealth University, and Winston-Salem State University.
Recent Publications
Selected publications (see site for complete list):
Design, Synthesis, and in vitro Evaluation of Aza-peptide Aldehydes and Ketones as Novel and Selective Protease Inhibitors
Corrigan, T. S.; Lotti Diaz, L. M.; Border, S. E.; Ratigan, S. C.; Kasper, K. Q.; Sojka, D.; Fajtova, P.; Caffrey, C. R.; Salvesen, G. S.; McElroy, C. A.; Hadad, C. M.; Dogan Ekici, O.
J. Enz. Inhib. Med. Chem. 2020, 35, 1387 – 1402.
DOI: 10.1080/14756366.2020.1781107
Insights on Absolute and Relative Stereocontrol in Stereodivergent Cooperative Catalysis
Changotra, A.; Bhaskararao, B.; Hadad, C. M.; Sunoj, R. B.
J. Am. Chem. Soc. 2020, 142, 9612 – 9624.
DOI: 10.1021/jacs.9b13962
[Mo2O2S8]2– Small Molecule Dimer as a Basis for Hydrogen Evolution Reaction (HER) Catalyst Materials
Chirdon, D. N.; Lalisse, R. F.; Sun, J.; Zhang, S.; Garrett, B. R.; Hadad, C. M.; Wu, Y.
SN Appl. Sci. 2020, 2, 889.
DOI: 10.1007/s42452-020-2706-3
A Novel, Modified Human Butyrylcholinesterase Catalytically Degrades the Chemical Warfare Nerve Agent, Sarin
McGarry, K. G.; Lalisse, R. F.; Moyer, R. A.; Johnson, K. M.; Tallan, A. M.; Winters, T. P.; Taris, J. E.; McElroy, C. A.; Lemmon, E. E.; Shafaat, H. S.; Fan, Y.; Deal, A.; Marguet, S. C.; Harvilchuck, J. A.; Hadad, C. M.; Wood, D. W.
Toxicol. Sci. 2020, 174, 133 – 146.
DOI: 10.1093/toxsci/kfz251
Twist-Turn-Twist Motif Chaperoned Inside Molecular Baskets
Pavlovic, R. Z.; Border, S. E.; Finnegan, T. J.; Zhiquan, L.; Gunther, M. J.; Munoz, E.; Moore, C. E.; Hadad, C. M.; Badjic, J. D.
J. Am. Chem. Soc. 2019, 141, 16600 – 16604.
DOI: 10.1021/jacs.9b09003
pH-Controlled Chiral Packing and Self-Assembly of a Coumarin Tetrapeptide
Mason, M. L.; Lalisse, R. F.; Finnegan, T. J.; Hadad, C. M.; Modarelli, D. A.; Parquette, J. R.
Langmuir 2019, 35, 12460 – 12468.
DOI: 10.1021/acs.langmuir.9b01939
Multivalent C-H···Cl/Br-C Interactions Directing the Resolution of Dynamic and Twisted Capsules
Pavlovic, R. Z.; Zhiquan, L.; Güney, M.; Lalisse, R. F.; Hopf, R. G.; Gallucci, J.; Moore, C.; Xie, H.; Hadad, C. M.; Badjic, J. D.
Chem. Eur. J. 2019, 25, 1 – 8.
DOI: 10.1002/chem.201903006
Hypercoordinate Iodine for Catalytic Asymmetric Diamination of Styrene: Insights into the Mechanism, Role of Solvent and Stereoinduction
Sreenithya, A.; Hadad, C. M.; Sunoj, R. B.
Chem. Sci. 2019, 10, 7082 – 7090.
DOI: 10.1039/C9SC01513B
Stereo- and Regioselective Synthesis of Molecular Baskets
Gunther, M. J.; Pavlovic, R. Z.; Fernandez, J. P.; Zhiquan, L.; Gallucci, J.; Hadad, C. M.; Badjic, J. D.
J. Org. Chem. 2019, 84, 4392 – 4401.
DOI: 10.1021/acs.joc.9b00330
Resurrection and Reactivation of Acetylcholinesterase and Butyrylcholinesterase
Franjesevic, A. J.; Sillart, S. B.; Beck, J. M.; Vyas, S.; Callam, C. S.; Hadad, C. M.
Chem. Eur. J. 2019, 25, 5337 – 5371.
DOI: 10.1002/chem.201805075
Johnson, E. M.; Waggoner, A. R.; Xia, S.; Luk, H. L.; Hadad, C. M.; Poole, J. S. Reactivity of Hydroxyl Radical in Nonaqueous Phases: Addition Reaction. J. Phys. Chem. A 2018, 122, 8326 – 8335.
Du, L.; Lan, X.; Phillips, D. L.; Coldren, W. H.; Hadad, C. M.; Yang, X.; Thamattoor, D. M. Direct Observation of an Alkylidenecarbene by Ultrafast Transient Absorption Spectroscopy. J. Phys. Chem. A 2018, 122, 6852 – 6855.
Zhuang, Q.; Franjesevic, A. J.; Corrigan, T. S.; Coldren, W. H.; Dicken, R.; Sillart, S.; DeYong, A.; Yoshino, N.; Smith, J.; Fabry, S.; Fitzpatrick, K.; Blanton, T. G.; Joseph, J.; Yoder, R. J.; McElroy, C. A.; Dogan Ekici, O.; Callam, C. S.; Hadad, C. M. Demonstration of In Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents. J. Med. Chem. 2018, 61, 7034 − 7042.
Feng, C.; Chan, D.; Joseph, J.; Muuronen, M.; Coldren, W. H.; Dai, N.; Corrêa, I. R., Jr.; Furche, F.; Hadad, C. M.; Spitale, R. C. Light Activated Chemical Probing of Nucleobase Solvent Accessibility Inside Cells. Nature Chemical Biology 2018, 14, 276 – 283.
Garrett, B. R.; Polen, S. M.; Pimplikar, M.; Hadad, C.M.; Wu, Y. Anion-Redox Mechanism of MoO(S2)2(2,2’-bipyridine) for Electrocatalytic Hydrogen Production. J. Am. Chem Soc. 2017, 139, 4342-4345.
Yu, Y.; Click, K. A.; Polen, S. M.; He, M.; Hadad, C. M.; Wu, Y. Electron Transfer Kinetics of a Series of Bilayer Triphenylamine-Oligothiophene-Perylenemonoimide Sensitizers for Dye-Sensitized NiO. J. Phys. Chem. C. 2017, 121, 20720−20728.
Zhiquan, L.; Polen, S. M.; Hadad, C. M.; RajanBabu, T.V.; Badjic, J. D. Examining the Scope and Thermodynamics of Assembly in Nesting Complexes Comprising Molecular Baskets and TPA Ligands. Org. Lett. 2017, 19, 4932-4935.
Sreenithya, A.; Patel, C.; Hadad, C.M.; Sunoj, R.B. Hypercoordinate Iodine Catalysts in Enantioselective Transformation: The Role of Catalyst Folding in Stereoselectivity. ACS Catal. 2017, 7, 4189-4196.
Yoder, R. J.; Zhuang, Q.; Beck, J. M.; Franjesevic, A.; Blanton, T. G.; Sillart, S.; Secor, T.; Guerra, L.; Brown, J. D.; Reid, C.; McElroy, C. A.; Doğan Ekici, Ö.; Callam, C. S.; Hadad, C.M. Study of para-Quinone Methide Precursors toward the Realkylation of Aged Acetylcholinesterase. ACS Med. Chem. Lett. 2017, 8, 622-627.
Garrett, B. R.; Click, K. A.; Durr, C. B.; Hadad, C.M.; Wu, Y. [MoO(S2)2L]1-(L= picolinate or pyrimidine-2-carboxylate) Complexes as MoSx Inspired Electrocatalysts for Hydrogen Production in Aqueous Solution. J. Am. Chem. Soc. 2016, 136, 13726–13731.
Pratumyot, Y.; Chen, S.; Hu, L.; Polen, S. M.; Hadad, C. M.; Badjic, J. D. Assembly and Folding of Twisted Baskets in Organic Solvents. Org. Lett. 2016, 18, 4238-4241.
Garrett, B. R.; Awad, A.; He, M.; Click, K. A.; Durr, C. B.; Gallucci, J. C.; Hadad, C. M.; Wu, Y. Dimeric FeFe-Hydrogenase Mimics Bearing Carboxylic Acids: Synthesis and Electrochemical Investigation. Polyhedron. 2016, 103, 21-27.
Zhuang, Q.; Young, A.; Callam, C. S.; McElroy, C. A.; Doğan Ekici, Ö.; Yoder, R. J.; Hadad, C.M. Efforts Toward Treatments Against Aging of Organophosphorus-inhibited Acetylcholinesterase. Ann. N. Y. Acad. Sci. 2016, 120, 7294-7300.
Korvinson, K. A.; Hargenrader, G. N.; Stevanovic, J.; Xie, Y.; Joseph, J.; Maslak, V.; Hadad, C. M.; Glusac, K. D. Improved Flavin-Based Catalytic Photooxidation of Alcohols through Intersystem Crossing Rate Enhancement. J. Phys. Chem. A. 2016, 1374, 94-104.
Walpita, J.; Yang, X.; Khatmullin, R.; Luk, H. L.; Hadad, C.M.; Glusac, K. D. Pourbaix Diagrams in Weakly Coupled Systems: A Case Study Involving Acridinol and Phenanthridinol Pseudobases. J. Phys. Org. Chem. 2016, 29, 204-208.
Zhiquan, L.; Polen, S.; Hadad, C. M.; RajanBabu, T. V.; Badjic, J. D. Russian Nesting Doll Complexes of Molecular Baskets and Zinc Containing TPA Ligands. J. Am. Chem. Soc. 2016, 138, 8253-8258.
Garrett, B. R.; Polen, S. M.; Click, K. A.; He, M.;Huang, Z.; Hadad, C. M.; Wu, Y. Tunable Molecular MoS2 Edge-Site Mimics for Catalytic Hydrogen Production. Inorg. Chem. 2016, 55, 3960−3966.
Chen, S.; Polen, S. M.; Wang, L.; Makoto, Y.; Hadad C.M.; Badjic, J.D. Two-Dimensional Supramolecular Polymers Embodying Large Unilamellar Vesicles in Water. J. Am. Chem. Soc. 2016, 138, 11312-11317.