COVID-19: Essential Information

Rick Bunt

Assoc. Dean of the Sciences; Joseph Burr Prof of Chem/Biochem

 work(802) 443-2559
 Fall 2021: MW 12:30-2:00
 McCardell Bicen Hall 550

Our research is motivated by a desire to understand how catalytic process occur at the detailed molecular level. In particular, we study palladium-catalyzed allylic-addition reactions and explore the functioning of chiral ligands. We are most interested in how three-dimensional “chiral information” is transmitted from the ligand, across the metal, to the reacting centers. We employ a combination of organic synthesis, physical organic methods, and one and two dimensional NMR spectroscopy, to study these reactions.

A series of chiral phosphinooxazoline (PHOX) ligands containing electron donating and withdrawing groups on the aryl backbone have been synthesized. The effects of these electronic perturbations are determined by measuring the enantiomeric excess of the alkylation and amination reaction products by chiral HPLC and by measuring the changes in the 13C NMR chemical shifts of the isolated p-allylpalladium intermediate complexes on the department's 400 MHz NMR spectrometer. The observed effects are then mathematically correlated to the electronic perturbations via Hammett and other types of linear free-energy relationship (LFER) analyses of the data.



Course List: 

Courses offered in the past four years.
indicates offered in the current term
indicates offered in the upcoming term[s]

CHEM 0103 - General Chemistry I      

General Chemistry I
Major topics will include atomic theory and atomic structure; chemical bonding; stoichiometry; introduction to chemical thermodynamics. States of matter; solutions and nuclear chemistry. Laboratory work deals with testing of theories by various quantitative methods. Students with strong secondary school preparation are encouraged to consult the department chair for permission to elect CHEM 0104 or CHEM 0107 in place of this course. CHEM 0103 is also an appropriate course for a student with little or no prior preparation in chemistry who would like to learn about basic chemical principles while fulfilling the SCI or DED distribution requirement. 3 hrs. lect., 3 hrs. lab, 1 hr. disc. DED SCI

Spring 2018

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CHEM 0203 - Organic I: Struct & Reactivity      

Organic Chemistry I: Structure and Reactivity
In Fall 2020, this course will be taught remotely using “flipped class” pedagogy. Students will be expected to watch videos prior to class, and classroom time will be dedicated to small group problem solving with faculty guidance. The course will provide students with an introduction to the structure and reactivity of organic molecules sufficient to continue directly to study of biochemistry (CHEM 0322). Topics covered will include models of chemical bonding, acid-base relationships, three-dimensional molecular structure (conformations and stereochemistry), reaction mechanisms and energy diagrams, substitution and elimination reactions, carbonyl reactions (additions, reductions, interconversions, and alpha-reactivity), and the fundamentals of biological molecules (carbohydrates, DNA, and RNA). Remote laboratory experiments will relate to purification techniques (recrystallization, distillation, extraction, and chromatography) as well as microscale organic reactions that complement the lecture portion of the course. (CHEM 0104 or CHEM 0107) 3 hrs. lect., 3 hrs. lab SCI

Spring 2018, Fall 2018, Spring 2019, Spring 2020, Fall 2021

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CHEM 0204 - Organic II: Synthesis & Spect      

Organic Chemistry II: Synthesis and Spectroscopy
In this course we will explore the ways that organic molecules are made and their structures identified. The study of organic reactions will continue from CHEM 0203 with radical reactions, alkene and alkyne additions, aromatic reactions, oxidations and reductions, and additional carbonyl reactions. Emphasis in this course will be placed on using reactions in sequences to synthesize larger and more complex molecules. The theory and practice of mass spectrometry and UV-Vis, IR, and NMR spectroscopy will be studied as a means to elucidate the exact structures of organic molecules. Laboratory experiments will focus on synthetic techniques that complement the lecture portion of the course and the identification of complex unknowns via GC-MS, IR, and NMR. (CHEM 0203) 3 hrs. lect., 3 hrs. lab, 1 hr. prelab.

Fall 2020, Spring 2021

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CHEM 0301 - Medicinal Chemistry      

Medicinal Chemistry
Medicinal chemistry combines organic chemistry with biochemistry, analytical chemistry, physical chemistry, molecular biology, pharmacology, and medicine. As chemists we try to correlate the molecular structure of pharmaceutical treatments (i.e., "drugs") with their biological activity to understand disease and to develop both new and improved treatments. In this course we will survey the major categories of diseases, drug targets, and drugs using a case-study approach. In addition to mid-term exams and a shorter group presentation on a disease category, the course will culminate with group-based final projects (presentation and written paper) about the design, development, and proposed future directions of treatments targeting a specific disease. (CHEM 0204 or CHEM 0322) 3 hrs. lect.

Spring 2022, Spring 2023

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CHEM 0311 - Instrumental Analysis      

Instrumental Analysis
This course introduces fundamental concepts of analytical chemistry, instrumental analysis, and scientific writing. Lecture topics include experimental design and quality control; sample collection and preparation; calibration, error, and data analysis; statistics; and the theory and operation of chemical instrumentation. Multi-week laboratory projects provide hands-on experience in qualitative and quantitative analysis using a variety of research-quality instrumentation (e.g., graphite furnace atomic absorption spectroscopy, UV/Vis spectrometry, gas chromatography mass spectrometry, circular dichroism spectroscopy, high pressure liquid chromatography). Writing workshops promote professional scientific writing skills through guided practice in writing analysis, peer review, and revision. For Fall 2020, hands-on skill development emphasized despite remote instruction using “lab kits” (all food grade, safe materials) sent to all students, with encouraged in-person options for students residing on-campus, as safety allows. (CHEM 0204 or CHEM 0242) 3 hr. lect., 6 hrs. lab. CW

Fall 2018, Fall 2019

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CHEM 0500 - Independent Study      

Independent Study Project
Individual study for qualified students. (Approval required)

Winter 2018, Spring 2018, Fall 2018, Winter 2019, Spring 2019, Fall 2019, Winter 2020, Spring 2020, Fall 2020, Winter 2021, Spring 2021, Fall 2021, Winter 2022, Spring 2022, Fall 2022, Winter 2023, Spring 2023

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CHEM 0700 - Senior Research      

Senior Research
In this course students complete individual projects involving laboratory research on a topic chosen by the student and a faculty advisor. Prior to registering for CHEM 0700, a student must have discussed and agreed upon a project topic with a faculty member in the Chemistry and Biochemistry Department. Attendance at all Chemistry and Biochemistry Department seminars is expected. (Approval required; open only to seniors)

Winter 2018, Spring 2018, Fall 2018, Winter 2019, Spring 2019, Fall 2019, Winter 2020, Spring 2020, Fall 2020, Winter 2021, Spring 2021, Fall 2021, Winter 2022, Spring 2022, Fall 2022, Winter 2023, Spring 2023

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CHEM 0701 - Senior Thesis      

Senior Thesis
Students who have initiated research projects in CHEM 0400 and who plan to complete a senior thesis should register for CHEM 0701. Students are required to write a thesis, give a public presentation, and defend their thesis before a committee of at least three faculty members. The final grade will be determined by the department. Attendance at all Chemistry and Biochemistry Department seminars is expected. (CHEM 0400; approval required)

Winter 2018, Spring 2018, Fall 2018, Winter 2019, Spring 2019, Fall 2019, Winter 2020, Spring 2020, Fall 2020, Winter 2021, Spring 2021, Fall 2021, Winter 2022, Spring 2022, Fall 2022, Winter 2023, Spring 2023

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MBBC 0700 - Senior Research      

Senior Thesis
Seniors conducting independent study in Molecular Biology and Biochemistry should register for MBBC 0700 unless they are completing a thesis project in which case they should register for MBBC 0701. (Approval required).

Fall 2018, Fall 2019, Fall 2020, Winter 2021, Fall 2021, Winter 2022, Fall 2022, Winter 2023

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MBBC 0701 - Senior Thesis      

Senior Thesis
Students conducting independent thesis research in Molecular Biology and Biochemistry must register for MBBC 0701 while completing research projects initiated in BIOL 0500, MBBC 0700, or CHEM 0400. Students will organize and lead regular discussions of their research and research methods, and attend weekly meetings with their designated laboratory group to foster understanding of their special area, and practice the stylistic and technical aspects of scientific writing needed to write their thesis. (CHEM 0400 or BIOL 0500 or MBBC 0700) (Approval required).

Winter 2018, Spring 2018, Fall 2021, Fall 2022

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Recent Awards

2007 Perkins Award for Excellence in Teaching

Recent Publications

Bryan S. Holtzman,# Eric T. Roberts,# Nicholas S. Caminiti,# Jacob A. Fox,# Madison B. Goodstein,# Staci A. Hill,# Zitong B. Jia,# Isabelle N. –M. Leibler,# Michael L. Martini,# Gina M. Mendolia,# Molly S. Costanza-Robinson, and Richard C. Bunt, Ligand and base additive effects on the reversibility of nucleophilic addition in palladium-catalyzed allylic aminations monitored by nucleophile crossover. Tetrahedron Lett. 2017, 58, 432.

*Nicholas S. Caminiti,*Madison B. Goodstein, *Isabelle N.-M . Leibler,*Bryan S. Holtzman, *Zitong B. Jia,  *Michael L. Martini, *Nathaniel C. Nelson,and Richard C. Bunt, Reversible nucleophilic addition can lower the observed enantioselectivity in palladium-catalyzed allylic amination reactions with a variety of chiral ligands. Tetrahedron Lett. 2015, 56, 5445.

Richard C. Bunt, Charlotte Majerczyk, Mitchell Brittnacher, Michael Jacobs, Christopher Armour, Matthew Radey, Hillary Hayden, Ryland Bydalek, and E. Peter Greenberg, “A cross-species comparison of the Burkholderia pseudomallei, Burkholderia thailandensis, and Burkholderia mallei quorum sensing regulons,” Journal of Bacteriology 2014, 196, 22, 3862.

Richard C. Bunt, Charlotte Majerczyk, Mitchell Brittnacher, Michael Jacobs, Christopher D. Armour, Mathew Radey, Emily Schneider, Somsak Phattarasokul, and E. Peter Greenberg, “Global Analysis of the Burkholderia thailandensis Quorum Sensing-Controlled Regulon,” Journal of Bacteriology, 2014, 196, 7, 1421.

Charlotte Majerczyk, Mitchell Brittnacher, Michael Jacobs, Christopher D. Armour, Mathew Radey, Emily Schneider, Somsak Phattarasokul, Richard Bunt and E. Peter Greenberg “Global Analysis of the Burkholderia thailandensis Quorum Sensing-Controlled Regulon” J. Bacteriol. 2014, 196, 7, 1412.

Charlotte Majerczyk, Loren Kinman, Tony Han, Richard Bunt, and E. Peter Greenberg “Virulence of Burkholderia mallei Quorum-Sensing Mutants” Infect. Immun. 2013, 81, 5, 1471.

*Armstrong, P.B., *Dembicer, E.A., *Desbois, A.J., *Fitzgerald, J.T., *Gehrmann, J.K., *Nelson, N.C., *Noble, A.L., Bunt, R.C. “Investigation of the Electronic Origin of Asymmetric Induction in Palladium-Catalyzed Allylic Substitutions with Phosphinooxazoline (PHOX) Ligands by Hammett and
Swain–Lupton Analysis of the 13C NMR Chemical Shifts of the (π-Allyl)palladium Intermediates.” Organometallics 2012, 31, 6933-6946. DOI: 10.1021/om3007163

Paul B. Armstrong,# Lisa M. Bennett, Ryan N. Constantine,# Jessica L. Fields,# Jerry P. Jasinski, Richard J. Staples, Richard C. Bunt "Hammett 13C NMR and X-ray studies of allylpalladium phosphinooxazoline chiral ligand complexes", Tetrahedron Lett. 2005, 46, 1441-1445.

Sunhee Choi, Richard B. Cooley,# Amanda S. Hakemian, # Yuna C. Larrabee, Richard C. Bunt, Stéphane D. Maupas, James G. Muller, and Cynthia J. Burrows, "Mechanism of Two-Electron Oxidation of Deoxyguanosine 5'-Monophosphate by a Platinum(IV) Complex" J. Am. Chem. Soc. 2004, 126, 591.

Ryan N. Constantine,# Naomi Kim,# and Richard C. Bunt, "Hammett Studies of Enantiocontrol by PHOX Ligands in Pd-Catalyzed Allylic Substitution Reactions" Org. Lett. 2003, 5, 2279.


2007 American Chemical Society-Petroleum Research Fund, "Hammett Studies of P,N-Chiral Ligands." 9/1/07- 8/31/10 ($55,000)

2007 National Science Foundation (NSF-RUI, CHE-0714541) "Hammett Studies of P,N-Chiral Ligands.", 8/15/07- 8/14/10 ($146,000)

2005 Vermont Genetics Network (NIH-BRIN), Equipment Grant for "A Solvent Purification System" Co-PI with Jeff Byers ($24,700)

2003 National Institutes of Health (NIH-AREA), "Mechanism of Base-Flipping by DNA Modifying Enzymes" ($137,971)

2003 Pfizer Summer Undergraduate Research Fellowship for Sarah S. Goodwin ($5,000)

2002 Vermont Genetics Network (NIH-BRIN), Partial Sabbatical Leave Support for "Altering the Rate of Base Flipping in DNA" ($20,000) 

2001 American Chemical Society-Petroleum Research Fund, Type G, "Probing the Electronic Origins of Chiral Ligand Asymmetry in Palladium-Catalyzed Allylic-Alkylation Reactions" ($25,000)

2001 Cottrell College Science Award from Research Corporation, "Probing the electronic origins of chiral ligand asymmetry in palladium-catalyzed allylic-aklylation reactions" ($41,381)

2000 Pfizer Summer Undergraduate Research Fellowship for Agnes Makingwe ($5,000)

2000 VT EPSCoR Award, "Electronic Control of Chiral Ligand Asymmetry" ($5,500)


Department of Chemistry & Biochemistry

McCardell Bicentennial Hall
276 Bicentennial Way
Middlebury College
Middlebury, VT 05753