Research Interests
Conformational preferences of furanoside carbohydrate derivatives using NMR and computation
Stereoselectivity in carbohydrate analogs
New labs that incorporate carbohydrate derivatives and analogs into the organic chemistry course
New labs that incorporate computational chemistry into many steps of the lab sequence for a chemistry degree
Education/Academic Qualifications
Ph.D., The Ohio State University
M.S., The Ohio State University
A.B., William Jewell
Conformational Preferences of Pentofuranosides
Bacteria that cause diseases such as tuberculosis and leprosy use unique carbohydrates as part of their natural defenses. Since these carbohydrates are not used in mammalian cells, they are natural targets for new antibiotics. The very flexible shapes of these carbohydrates are not well understood. A better understanding of the flexible shape, or conformational preference, of these carbohydrates will strengthen our ability to design these new antibiotics. This is especially important because many of these bacteria are developing multiple-drug-resistant strains.
Research in the Rhoad group falls into two categories: computational and synthetic/spectroscopic. Our computational methods build models that are designed to predict the conformational preference of the simple protected sugars. The synthetic/spectroscopic derivatizes simple sugars and then does close measurements of the parameters influenced by the conformation—specifically proton-proton coupling constants in nuclear magnetic resonance spectroscopy. The measured versus calculated parameters are compared to determine the success of the computational modelling.
Publications
Rhoad, J. (2011). Determination of Relative Stereochemistry of an Unknown Carbohydrate: Application of Two-dimensional NMR and the Karplus Relationship. The Chemical Educator, 16(DOI 10.1007/s00897102398a), 304-306. chemeducator.org/bibs/0016001/16100304.htm
Rhoad, J., Cagg, B. A., Carver, P. W. (2010). Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Glycosylation Reactions. Journal of Physical Chemistry A, 114(15), 5180-5186.
Rhoad, J., Lowary, T. L., Ferguson, M. J. (2004). ³4,8-anhydro-1,2,3,5-tetradeoxy-D-allo-non-1-enitol². Acta Crystallographica E, E60, o1942-o1944.
Rhoad, J., Lowary, T. L., Ferguson, M. J. (2004). ³5,6,7,9-Tetra-O-acetyl-4,8-anhydro-1,2,3-trideoxy-D-glycero-D-gulo-non-1-enitol. Acta Crystallographica E, E60, o1939-o1941.
Rhoad, J., Evaluating the evidence: Determining the course of a Diels-Alder reaction using visible spectroscopy. The Chemical Educator (2026) 31(1):107. https://doi.org/10.1525/tce.2026.107
Culver S., Rhoad, J. S. Acetyl α-D-2,3,4-triacetyllyxopyranoside (2025). IUCrData 10, x250016
https://doi.org/10.1107/S2414314625000161
Rhoad, J. Written Assignments in Organic Chemistry: Critical Reading and Creative Writing (2016). The Journal of Chemical Education, 94(3), 267-270. DOI: 10.1021/acs.jchemed.6b00402
Rahman, P., Glanzer, A., Singh, J., Wachter, N.M., Rhoad, J., Denton, R.W. Solvent Effects on the [3+2] Cycloaddition of 2-Furfural Oxime and Ethyl Propiolate: Unexpected Change in Regioselectivity (2017). World Journal of Organic Chemistry. 5(1), 6-10. DOI: 10.12691/wjoc-5-1-2
Rhoad, J. Written Assignments in Organic Chemistry: Critical Reading and Creative Writing (2016). The Journal of Chemical Education, 94(3), 267-270. DOI: 10.1021/acs.jchemed.6b00402
Torres y Torres, J., Hiley, S., Lorimor, S., Rhoad, J., Caldwell, B., Zweerink, G., Ducey, M. (2015). Separation and Analysis of Caffeine from Beverages using Thin-Layer Chromatography and Gas Chromatography-Mass Spectroscopy. Journal of Chemical Education, 92(5), 900-902. pubs.acs.org/doi/abs/10.1021/ed500977r
Presentations
Rhoad, J. (Author Only), Freeman, D. (Presenter & Author), Cassity, A. (Author Only), Spring 2013 National Convention, “A Comparison Between Computational Conformational Populations and NMR J-value Coupling in Permethylated Pentafuranosides,” American Chemical Society, New Orleans, LA. (April 8, 2013).
Rhoad, J. (Author Only), Freeman, D. (Author Only), Cassity, A. (Presenter & Author), Spring 2013 National Convention, “Improved Understanding of Conformational Preferences of Permethylated Furanosides,” American Chemical Society, New Orleans, LA. (April 8, 2013).
Rhoad, J. (Author Only), Edlin, M. (Presenter & Author), Spring 2013 National Convention, “Multiple Step Synthesis of 2-deoxy-glycero-tetrose for Organic Chemistry Labs: Applications in Carbohydrate Stereochemistry,” American Chemical Society, New Orleans, LA. (April 8, 2013).
Rhoad, J. (Presenter & Author), Spring 2013 National Convention, “Evaluating the evidence: Determining the course of a Diels-Alder reaction using visible spectroscopy,” American Chemical Society, New Orleans, LA. (April 7, 2013).
Rhoad, J. (Author Only), Dow, B. (Presenter & Author), Ruark, C. (Author Only), Spring 2011 National Convention, “A New Method for Scanning Furanose Potential Energy Surfaces: Applications in Carbohydrate Chemistry,” American Chemical Society, Anaheim, CA. (March 28, 2011).
Rhoad, J. (Presenter & Author), Dow, B. (Author Only), Ruark, C. (Author Only), Spring 2011 National Convention, “A New Method for Scanning Furanose Potential Energy Surfaces: Applications in Carbohydrate Chemistry,” American Chemical Society, Anaheim, CA. (March 28, 2011).
Rhoad, J. (Author Only), Edlin, M. (Presenter & Author), Spring 2011 National Convention, “New multistep synthesis for organic chemistry labs:,” American Chemical Society, Anaheim, CA. (March 28, 2011).
Rhoad, J. (Author Only), Cagg, B. A. (Presenter & Author), Carver, P. W. (Author Only), ACS Spring National Convention, ““Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Carbohydrate Reactions”,” American Chemical Society, Salt Lake City, UT. (2009).
Rhoad, J. (Presenter & Author), Cagg, B. A. (Author Only), Carver, P. W. (Author Only), ACS Fall National Convention, ““Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Carbohydrate Reactions”,” American Chemical Society, Philadelphia, PA. (2008).
Rhoad, J. (Presenter & Author), Cagg, B. A. (Author Only), Carver, P. W. (Author Only), ACS Spring National Convention, ““Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Carbohydrate Reactions”,” American Chemical Society, New Orleans, LA. (2008).
Rhoad, J. (Author Only), Cagg, B. A. (Presenter & Author), Carver, P. W. (Author Only), ACS Midwest Regional Meeting, ““Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Carbohydrate Reactions”,” American Chemical Society, Kansas City, MO. (2007).
Rhoad, J. (Presenter & Author), Cagg, B. A. (Author Only), Carver, P. W. (Author Only), ACS Midwest Regional Meeting, ““Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Carbohydrate Reactions”,” American Chemical Society, Kansas City, MO. (2007).
Houseknecht, J. B. (Author Only), Rhoad, J. (Author Only), Tao, P. (Author Only), DeMatteo, M. P. (Author Only), Sunoj, R. B. (Author Only), McCarren, P. R. (Author Only), Callam, C. S. (Author Only), Hada, C. M. (Author Only), Lowary, T. L. (Presenter & Author), ACS National Convention, “”Conformational Investigations of Arabinofuranosyl Oligosaccharides from Mycobacteria”,” American Chemical Society. (2004).
Rhoad, J. (Presenter & Author), Turro, C. (Author Only), Lowary, T. L. (Author Only), Alberta Ingenuity Center Carbohydrate Conference, “”Synthesis of Saccharides for the Binding of Dirhodium to DNA”,” Alberta Ingenuity Center, Banff, Alberta, Canada. (2003).
Rhoad, J. (Presenter & Author), Turro, C. (Author Only), Lowary, T. L. (Author Only), Gordon Conference on Carbohydrate Chemistry, “”Synthesis of Saccharides for the Binding of Dirhodium to DNA”,” Gordon Conferences, New Hampshire. (June 2003).
Rhoad, J. (Presenter & Author), Turro, C. (Author Only), Lowary, T. L. (Author Only), ACS Spring National Convention, “”Synthesis of Saccharides for the Binding of Dirhodium to DNA”,” American Chemical Society. (2001).
Jonathan Rhoad, 251st National Meeting of the American Chemical Society, “Studies in the conformational preferences of flexible monosaccharides,” American Chemical Society, Atlanta, GA. (March 2026).
Ducey, A. (Presenter & Author), Rhoad, J. (Author Only), 251st National Meeting of the American Chemical Society, “Synthesis and Characterization of a Monofluorinated Carbohydrate Derivative,” American Chemical Society, Atlanta, GA. (March 2026).
Beck, A. (Presenter & Author), Rhoad, J. (Author Only), 251st National Meeting of the American Chemical Society, “Synthesis and Characterization of a Difluorinated Carbohydrate Derivative,” American Chemical Society, Atlanta, GA. (March 2026).
Jonathan Rhoad, “Studies in the conformational preferences of flexible monosaccharides.” Presentation to the Conference on Applied Learning in Higher Education, Saint Joseph, MO on March 7, 2025.
Rhoad, J. (Presenter and Author), David Freeman (Author Only), Darien Morrow (Author Only), Shawn Culver (Author Only), Chris Holcomb (Author Only), Jennifer Dorris (Author Only) “Studies in the conformational flexibility of flexible monosaccharides.” Kansas City American Chemical Society Monthly Meeting, October 2023.
Rhoad, J. (Presenter and Author), David Freeman (Author Only), Darien Morrow (Author Only), Shawn Culver (Author Only), Chris Holcomb (Author Only), Jennifer Dorris (Author Only) “Studies in the conformational flexibility of flexible monosaccharides.” 251st National Meeting of the American Chemical Society, San Diego, CA on March 20, 2022.
Dorris, J. (Presenter and Author), Rhoad, J. (Author Only) “Synthesis of Methyl Triacetyl Xyloside.” PORTAL Symposium, September 10, 2021.
Rhoad, J. (Presenter and Author) “Studies in the conformational flexibility of flexible monosaccharides.” Presentation to the Missouri Academy of Science Annual Meeting, Columbia, MO on April 24, 2021.
Rhoad, J. (Presenter & Author), 2019 Midwest Regional Meeting of the American Chemical Society, “Using technology to our advantage: Tales from a partially flipped organic chemistry classroom,” American Chemical Society, Wichita, KS. (October 18, 2019).
Rhoad, J. (Presenter and Author) “Improved Understanding of Conformational Preferences of Peracetylated Furanosides.” Poster presented at the 255th National Meeting of the American Chemical Society, on March 20, 2018.
Rhoad, J. (Presenter & Author), Cooper, K. (Author Only), Edlin, M. (Author Only), Chapman N. (Author Only), 251st National Meeting of the American Chemical Society, “Incorporating Carbohydrates into Undergraduate Labs,” American Chemical Society, San Diego, CA. (March 2016).
Rhoad, J. (Author Only), Hunt, A. (Presenter & Author), 251st National Meeting of the American Chemical Society, “Energies and Conformational Preferences of Perfluoronated α-Furanoses,” American Chemical Society, San Diego, CA. (March 2016).
Rhoad, J. (Presenter & Author), 2015 Midwest Regional Meeting, “Using written assignments in organic chemistry to guide students to better study habits,” American Chemical Society, Saint Joseph, MO. (October 23, 2015).
Barta, C. (Presenter & Author), Hatch, S. (Presenter & Author), Svojanovsky, S. (Author Only), Rhoad, J. (Author Only), Ducey, M. (Author Only), Eckdahl, T. (Author Only), Association of College and University Biology Educators, ACUBE, 2015, “Do multidisciplinary science camps enhance high school student learning and interest in pursuing a career in life-sciences?,” ACUBE, Saint Joseph, MO. (October 23, 2015).
Ducey, M. (Author Only), Myers, D. (Author Only), Rhoad, J. (Presenter & Author), Woodford, J. (Presenter & Author), 249th National Meeting of the American Chemical Society, “Computational modelling across the curriculum: General, organic and physical chemistry,” American Chemical Society, Denver, CO. (March 2015).
Rhoad, J. (Presenter & Author), Freeman, D. (Author Only), Cassity, A. (Author Only), Edlin, M. (Author Only), Ruark, C. (Author Only), Cagg, B. (Author Only), Dow, B. (Author Only), Quaney, M. (Author Only), Hunt, A. (Author Only), Spring 2014 National Convention, “Examining furanoside conformational preference and reactivity: Computation, synthesis, and NMR,” American Chemical Society, Dallas, TX. (March 18, 2014).
Rhoad, J. Organic Chemistry Division Departmental Seminar, “Examining Furanoside Conformational Preference and Reactivity,” University of Missouri, Columbia, MO. (October 14, 2013).
Awards
Compass Award, Alpha Chi Honor Society, Missouri Lambda Chapter. (December 10, 2025).
Compass Award, Alpha Chi Honor Society. (December 2013)
Honorable Mention, Critical Thinking Award, Dean’s Council. (April 2008).
Outstanding Instructor, Disability Services. (May 2007).
