@article{fourches_feducia_2019, title={Student-Guided Three-Dimensional Printing Activity in Large Lecture Courses: A Practical Guideline}, volume={96}, ISSN={["1938-1328"]}, DOI={10.1021/acs.jchemed.8b00346}, abstractNote={Modern technology stimulates the development of innovative classroom activities. We designed a 3D printing activity in two separate Organic Chemistry lectures of at least 200 students each. This assignment required students to 3D print a molecule of their choice, relying on services made available through the university libraries. Data obtained through a survey at the end of the semester provided key information on the students’ experiences with printing 3D models for the first time. A summary of this feedback and constructive remarks on the best practices regarding 3D printing assignments in large lecture courses are presented.}, number={2}, journal={JOURNAL OF CHEMICAL EDUCATION}, author={Fourches, Denis and Feducia, Jeremiah}, year={2019}, month={Feb}, pages={291–295} } @article{feducia_dumarieh_gilvey_smirnova_franzen_ghiladi_2009, title={Characterization of Dehaloperoxidase Compound ES and Its Reactivity with Trihalophenols†}, volume={48}, ISSN={0006-2960 1520-4995}, url={http://dx.doi.org/10.1021/bi801916j}, DOI={10.1021/bi801916j}, abstractNote={Dehaloperoxidase (DHP), the oxygen transport hemoglobin from the terebellid polychaete Amphitrite ornata, is the first globin identified to possess a biologically relevant peroxidase activity. DHP has been shown to oxidize trihalophenols to dihaloquinones in a dehalogenation reaction that uses hydrogen peroxide as a substrate. Herein, we demonstrate that the first detectable intermediate following the addition of hydrogen peroxide to ferric DHP contains both a ferryl heme and a tyrosyl radical, analogous to Compound ES of cytochrome c peroxidase. Furthermore, we provide a detailed kinetic description for the reaction of preformed DHP Compound ES with the substrate 2,4,6-trichlorophenol and demonstrate the catalytic competency of this intermediate in generating the product 2,4-dichloroquinone. Using rapid-freeze-quench electron paramagnetic resonance spectroscopy, we detected a g approximately 2.0058 signal confirming the presence of a protein radical in DHP Compound ES. In the absence of substrate, DHP Compound ES evolves to a new species, Compound RH, which is functionally unique to dehaloperoxidase. We propose that this intermediate plays a protective role against heme bleaching. While unreactive toward further oxidation, Compound RH can be reduced and subsequently bind dioxygen, generating oxyferrous DHP, which may represent the catalytic link between peroxidase and oxygen transport activities in this bifunctional protein.}, number={5}, journal={Biochemistry}, publisher={American Chemical Society (ACS)}, author={Feducia, Jeremiah and Dumarieh, Rania and Gilvey, Lauren B. G. and Smirnova, Tatyana and Franzen, Stefan and Ghiladi, Reza A.}, year={2009}, month={Feb}, pages={995–1005} } @article{feducia_gagné_2008, title={Reversibility Effects on the Stereoselectivity of Pt(II)-Mediated Cascade Poly-ene Cyclizations}, volume={130}, ISSN={0002-7863 1520-5126}, url={http://dx.doi.org/10.1021/ja075518i}, DOI={10.1021/ja075518i}, abstractNote={Cyclization of 1,5-dienes bearing nucleophilic traps with electrophilic trisphosphine pincer ligated Pt(II) complexes results in the formation of a polycyclic Pt-alkyl via a Pt(eta2-alkene) intermediate. With electron-rich triphosphine ligands, an equilibrium between the Pt(eta2-alkene) and Pt-alkyl was observed. The position of the equilibrium was sensitive to ligand basicity, conjugate acid strength, solvent polarity, and ring size. In cases where the ligand was electron poor and did not promote retrocyclization, the kinetic products adhering to the Stork-Eschenmoser postulate were observed (E-alkenes give trans-ring junctions). When retrocyclization was rapid, alternative thermodynamic products resulting from multistep rearrangements were observed (cis-[6,5]-bicycles). Under both kinetic and thermodynamic conditions, remote methyl substituents led to highly diastereoselective reactions. In the case of trienol substrates, long-range asymmetric induction from a C-ring substituent was considerably attenuated and only modest diastereoselectivity was observed (approximately 2:1). The data suggest that for a tricyclization, the long-range stereocontrol results from diastereo-selecting interactions that develop during the organization of the nascent rings. In contrast, the bicyclization diastereoselectivities result from reversible cascade cyclization.}, number={2}, journal={Journal of the American Chemical Society}, publisher={American Chemical Society (ACS)}, author={Feducia, Jeremiah A. and Gagné, Michel R.}, year={2008}, month={Jan}, pages={592–599} } @article{feducia_campbell_doherty_gagné_2006, title={Modular Catalysts for Diene Cycloisomerization:  Rapid and Enantioselective Variants for Bicyclopropane Synthesis}, volume={128}, ISSN={0002-7863 1520-5126}, url={http://dx.doi.org/10.1021/ja064335d}, DOI={10.1021/ja064335d}, abstractNote={Deconstructing the tridentate (triphos)Pt(II) first-generation catalysts into mixed diphosphine/monophosphine combinations (P(2)P) has led to new, more active catalysts for the cycloisomerization of 1,6-, and 1,7-dienes into bicyclo-[3.1.0] and -[4.1.0] products. When the diphosphine was the small bite angle dppm, reaction rates were approximately 20-fold faster than with triphos, although reaction rates and diastereoselectivities were also sensitive to the monophosphine (PMe(3) being optimal for rate, PPh(3) being optimal for selectivity). When the diphosphine was xyl-BINAP or SEGPHOS, the catalysts were enantioselective, and enantio-ratios up to 98:2 were observed. Both sets of catalysts showed enhanced functional group tolerance in comparison to the original (triphos)Pt(2+) catalyst. X-ray structures for both precatalysts are also reported.}, number={40}, journal={Journal of the American Chemical Society}, publisher={American Chemical Society (ACS)}, author={Feducia, Jeremy A. and Campbell, Alison N. and Doherty, Michael Q. and Gagné, Michel R.}, year={2006}, month={Oct}, pages={13290–13297} } @article{feducia_campbell_anthis_gagné_2006, title={Protonolysis of Cationic Pt−C Bonds with Mild Acids:  Can Ligand Torsional Effects Speed Associative Processes?}, volume={25}, ISSN={0276-7333 1520-6041}, url={http://dx.doi.org/10.1021/om051066b}, DOI={10.1021/om051066b}, abstractNote={Tridentate phosphine pincer ligands facilitate the protonolysis of cationic Pt−CH3 compounds (to Pt dications and CH4) with the ammonium acid Ph2NH2·BF4. Large rate enhancements over nonpincer analogues (>50 000) are observed. A mechanism is proposed wherein ring strain present in the planar ground-state arrangement of three phosphine ligands is released in putative five-coordinate intermediates and transition states.}, number={13}, journal={Organometallics}, publisher={American Chemical Society (ACS)}, author={Feducia, Jeremy A. and Campbell, Alison N. and Anthis, Jeffrey W. and Gagné, Michel R.}, year={2006}, month={Jun}, pages={3114–3117} }