Ryan Groeneman | Webster University

Ryan Groeneman, PhD


  Browning Hall, ISB 335 
  (314) 968-7466



University of Missouri
Doctor of Philosophy Degree in Chemistry, December 2000

Southern Illinois University at Edwardsville
Bachelor of Science Degree in Chemistry, May 1996

Academic Appointments

Webster University
Professor, August 2016 - Present
Associate Professor, August 2012 - July 2016 

Jefferson College
Chair Mathematics, Science and Business Division, July 2011 – June 2012
Professor, August 2009 – June 2012
Associate Professor, August 2005 – July 2009
Assistant Professor, August 2001 – July 2005

Chemistry Courses Taught

Organic Chemistry I and II
Inorganic Chemistry
Concepts in Chemistry


(44) X. Ding, D.K. Unruh, R.H. Groeneman, and K.M. Hutchins, Controlling Thermal Expansion within Mixed Co-crystals by Tuning Molecular Motion Capability. Chemical Science 2020, 11, 7701.

(43) S.M. Oburn, C.L. Santana, E. Elacqua, and R.H. Groeneman, A diamondoid net sustained by halogen bonds: employing a cyclobutane to generate a tetrahedral architecture. CrystEngComm 2020, 22, 4349.

(42) E. Bosch, J.D. Battle, and R.H. Groeneman, Crystal structure and photoreactivity of a halogen-bonded cocrystal based upon 1,2-diiodoperchlorobenzene and 1,2-bis(pyridin-4-yl)ethylene. Acta Crystallographica Section C 2020, C76, 557.

(41) S.J. Kruse, E. Bosch, F. Brown, and R.H. Groeneman, Incorporating Ester Functionality within a Solid-State [2 + 2] Cycloaddition Reaction Based Upon Halogen Bonding Interactions. Crystal Growth and Design 2020, 20, 1969.

(40) N. Juneja, D.K. Unruh, E. Bosch, R.H. Groeneman, and K.M. Hutchins, Effects of dynamic pedal motion and static disorder on thermal expansion within halogen bonded co-crystals. New Journal of Chemistry 2019, 43, 18433.

(39) E. Bosch, S.J. Kruse, E.W. Reinheimer, N.P. Rath, and R.H. Groeneman, Regioselective [2 + 2] cycloaddition reaction within a pair of polymorphic co-crystals based upon halogen bonding interactions. CrystEngComm 2019, 21, 6671.

(38) S.M. Oburn, M.A. Sinnwell, D.P. Ericson, E.W. Reinheimer, D.M. Proserpio, R.H. Groeneman, and L.R. MacGillivray, Diversifying Molecular and Topological Space via a Supramolecular Solid-State Synthesis: A Purely Organic mok Net Sustained by Hydrogen Bonds. IUCrJ 2019, 6, 1032.

(37) A.L. Grobelny, N.P. Rath, and R.H. Groeneman, Varying the regiochemistry from a solid-state [2+2] cycloaddition reaction within a series of mixed co-crystals based upon isosteric resorcinols. Journal of Photochemistry and Photobiology A 2019, 382, 111966.

(36) E. Bosch, S.J. Kruse, H.R. Krueger, Jr., and R.H. Groeneman, Role of π-π Stacking and Halogen Bonding by 1,4-Diiodoperchlorobenzene to Organize the Solid State to Achieve a [2+2] Cycloaddition Reaction. Crystal Growth and Design 2019, 19, 3092. 

(35) A.L. Grobelny, N.P. Rath, and R.H. Groeneman, Regioselective Photoreactions within a Series of Mixed Co-crystals Containing Isosteric Dihalogenated Resorcinols with 4-Stilbazole. Photochemical & Photobiological Sciences 2019, 18, 989.

(34) A.W. Crawford, R.H. Groeneman, D.K. Unruh, and K.M. Hutchins, Cooling-rate dependent single-crystal-to-single-crystal phase transition in an organic co-crystal. Chemical Communications 2019, 55, 3258.

(33) E. Bosch, S.J. Kruse, and R.H. Groeneman, Infinite and discrete halogen bonded assemblies based upon 1,2-bis(iodoethynyl)benzene. CrystEngComm  2019, 21, 990.

(32) K.M. Hutchins, D.K. Unruh, and R.H. Groeneman, Covalent bond formation via a [2+2] cycloaddition reaction as a tool to alter thermal expansion parameters of organic co-crystals. New Journal of Chemistry 2018, 42, 16460.

(31) K.M. Hutchins, D.K. Unruh, D.D. Carpenter, and R.H. Groeneman, Thermal expansion along one-dimensional chains and two-dimensional sheets within co-crystals based on halogen or hydrogen bonds. CrystEngComm 2018, 20, 7232.

(30) G. Campillo-Alvarado, K. Aslan, M.A. Sinnwell, E.W. Reinheimer, S.V.S Mariappan, L.R. MacGillivray, and R.H. Groeneman, A Solid-State [2+2] Photodimerization Involving Coordination of Ag (I) Ions to 2-Pyridyl Groups. Journal of Coordination Chemistry 201871, 2875. 

(29) A.L. Grobelny, N.P. Rath, and R.H. Groeneman, Varying the regiochemistry of a [2+2] cycloaddition reaction within isostructural hydrogen bonded co-crystals containing 4-stilbazole. CrystEngComm 2018, 20, 3951. 

(28) K.M. Hutchins, S.P. Yelgaonkar, B.L. Harris-Conway, E.W. Reinheimer, L.R. MacGillivray, and R.H. Groeneman, Unlocking Pedal Motion of the Azo Group: Three- and Unexpected Eight-Component Hydrogen-Bonded Assemblies in Co-crystals Based on Isosteric Resorcinols. Supramolecular Chemistry 2018, 30, 533. 

(27) K.M. Hutchins, D.K. Unruh, F.A. Verdu, and R.H. Groeneman, Molecular Pedal Motion Influences Thermal Expansion Properties within Isostructural Hydrogen-Bonded Co-crystals. Crystal Growth and Design 201818, 566. 

(26) S.P. Fisher, R. Ramos, R.H. Groeneman, J.W. Kenney, III, and E.W. Reinheimer, Supramolecular interactions within a dual organometallic adduct based upon trimeric perfluoro-ortho-phenylenemercury and ferrocenecarboxaldehyde. Journal of Organometallic Chemistry 2017848, 239.

(25) K.M. Hutchins, J. Stojaković, R.H. Groeneman, and L.R. MacGillivray, Co-crystals for Solid-State Reactivity and Thermal Expansion in Multicomponent Solids: Synthesis, Concepts, Function. Editors Edward Tiekink and Julio Zukerman-Schpector, Walter de Gruyter, 2017

(24) A.L. Grobelny, F.A. Verdu, and R.H. Groeneman, Solvent-free synthesis and purification of a photoproduct via sublimation of a tetrahalogenated template. CrystEngComm 2017, 19, 3562. 

(23) C.M. Santana, E.W. Reinheimer, H.R. Krueger, Jr., L.R. MacGillivray, and R.H. Groeneman, Edge-to-Edge C-H∙∙∙N Hydrogen Bonds in Two-Component Co-crystals Aide a [2+2] Photodimerization. Crystal Growth and Design 2017, 17, 2054.

(22) K.M. Hutchins, K.A. Kummer, R.H. Groeneman, E.W. Reinheimer, M.A. Sinnwell, D.C. Swenson and L.R. MacGillivray, Thermal expansion properties of three isostructural co-crystals composed of isosteric components: interplay between halogen and hydrogen bonds. CrystEngComm 2016, 18, 8354.

(21) E. Elacqua, M.A. Sinnwell, B.P. Loren, P.T. Jurgens, R.H. Groeneman, E.W. Reinheimer, and L.R. MacGillivray, Metal-Organic Coordination Versus Hydrogen Bonding: Highly-Efficient Photocycloadditions of Conformationally-Frustrated Olefinic Isomers in Templated Solid-State Reactions. ChemPlusChem 201681, 893.

(20) M.A. Sinnwell, B.J. Ingenthron, R.H. Groeneman, and L.R. MacGillivray, Stereoselective and Quantitative [2+2] Photodimerization of a Symmetrical Octafluoro Stilbene in the Solid State: Face-to-Face Stacking of the Fluorinated Rings in trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene. Journal of Fluorine Chemistry 2016, 188, 5.

(19) E. Elacqua, K.A. Kummer, R.H. Groeneman, E.W. Reinheimer, and L.R. MacGillivray, Post-application of dry vortex grinding facilitates a near quantitative [2+2] photocycloaddition in the solid state: overcoming static disorder in a cocrystal using mechanochemistry. Journal of Photochemistry and Photobiology A 2016311, 42.

(18) S.P. Fisher, E.W. Reinheimer, and R.H. Groeneman, Arrays of Infinite and Discrete Non-Covalent Interactions in the Supramolecular Adduct Based upon Trimeric Perfluoro-ortho-Phenylenemercury and 9-Fluorenone. Polyhedron 2016, 114, 213. Invited Contribution “Undergraduate Research in Inorganic Chemistry”

(17) E.W. Reinheimer, A. Kohn, R.H. Groeneman, H.R. Krueger, Jr., K.A. Kantardjieff, and A.R. Johnson, Crystal Structures of D-N-(2-Adamantyl) phenylglycinol and L-N-(2-Adamantyl) diphenylphenylalinol: Chiral Amino Alcohols Utilized as Ligands for Catalytic Asymmetric Hydroamination. Molecular Crystals and Liquid Crystal 2016, 62970.

(16) S.P. Fisher, H.R. Krueger, Jr., R.H. Groeneman, and E.W. Reinheimer, Binary Supramolecular Adduct based upon Trimeric perfluoro-ortho-phenylenemercury and 4-Chlorobenzaldehyde: Enumerating the Strength of Perfluorophenyl- Perfluorophenyl Interactions. Journal of Molecular Structure 2016, 1103, 104.

(15) D.P. Ericson, Z.P. Zurfluh-Cunningham, R.H. Groeneman, E. Elacqua, E.W. Reinheimer, B.C. Noll, and L.R. MacGillivray. Regiocontrol of the [2+2] Photodimerization in the Solid State using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Dimeric Assemblies. Crystal Growth and Design 2015, 15, 5744.

(14) E. Elacqua, R.H. Groeneman, E.W. Reinheimer, and L.R. MacGillivray, Photostable Co-crystals of (E)-methyl-3-(pyridin-4-yl)prop-2-enoates Involving Isosteric Resorcinols: Effects of Secondary Interactions Involving Templates. Transactions of the American Crystallographic Association 2015, 45, 1.

(13) S.P. Fisher, R.H. Groeneman, and E.W. Reinheimer, Structural and Spectroscopic Analyses of a Ternary Supramolecular Complex [(o-C6F4Hg)3(o-Me2TTF)•CH3CN]: Elucidating and Validating Non-Covalent Interactions in the Solid State. Journal of Coordination Chemistry 2015, 68, 3589.

(12) E.W. Reinheimer, I. Hodzic, N.P. Rath, and R.H. Groeneman, Varying the Extended Packing of Silver(I) Ladder-Like Coordination Polymers by Modifying  the Organic Group of Various Organosulfonate Anions. Polyhedron 2015, 98, 105.

(11) K.M. Hutchins, R.H. Groeneman, E.W. Reinheimer, D.C. Swenson, and L.R. MacGillivray, Achieving dynamic behavior and thermal expansion in the organic solid state via co-crystallization. Chemical Science 2015, 6, 4717.

(10) D. Kimball, J. Starnes, R.H. Groeneman, H.R. Krueger, Jr., and E.W. Reinheimer, Two-dimensional sheet based upon C-H∙∙∙N hydrogen bonds within an organic co-crystal: a crystallographic, spectroscopic, and theoretical study. Supramolecular Chemistry 2015, 27, 465.

(9)   E. Elacqua, R.H. Groeneman, E.W. Reinheimer, D.-K. Bučar, and L.R. MacGillivray, Organosulfonates Aid Argentophilic Forces in the Crystal Engineering of [2+2] Photodimerizations: Reactivity Involving 3-Pyridyl Groups. Supramolecular Chemistry 2014, 26, 207.

(8)   E. Elacqua, P. Kaushik, R.H. Groeneman, D.-K. Bučar, J.C. Sumrak, and L.R. MacGillivray, A Supramolecular Protecting Group Strategy Introduced to the Organic Solid State: Enhanced Reactivity through Molecular Pedal Motion. Angewandte Chemie International Edition 2012, 51, 1037.

(7)   H.He, J.E. Morley, B.Twamley, R.H. Groeneman, D.-K. Bučar, L.R. MacGillivray, and P.D. Benny, Investigation of the Coordination Interactions of S-(Pyridin-2-ylmethyl)-L-Cysteine Ligands with M(CO)3+ (M= Re, 99mTc). Inorganic Chemistry 2009, 48, 10625.

(6)   R.H. Groeneman and J.L. Atwood, Controlling Aromatic Inclusion within Nonaqueous Copper Iodide Coordination Polymers. Supramolecular Chemistry 2001, 12, 353.

(5)   R.H. Groeneman and J.L. Atwood, Self-Assembly of a Novel One-Dimensional Zigzag Coordination Polymer. Supramolecular Chemistry 2000, 11, 251.

(4)   R.H. Groeneman and J.L. Atwood, Terephthalate Bridged Coordination Polymers of Group Two Metals. Crystal Engineering, 1999, 2, 241.

(3)   R.H. Groeneman, L.R. MacGillivray, and J.L. Atwood, One-Dimensional Coordination Polymers Based upon Bridging Terephthalate Ions. Inorganic Chemistry 1999, 38, 208.

(2)   R.H. Groeneman, L.R. MacGillivray, and J.L. Atwood, Aromatic Inclusion within a Neutral Cavity-Containing Rectangular Grid.  Chemical Communications 1998, 2735.

(1)   L.R. MacGillivray, R.H. Groeneman, and J.L. Atwood, Design and Self-Assembly of Cavity Containing Rectangular Grids.  Journal of the American Chemical Society  1998, 120, 2676.

Recent Presentations

-International Conference on the Chemistry of the Organic Solid State

  • R.H. Groeneman, S.J. Kruse, and E. Bosch, Organizing the Organic Solid State to Achieve [2+2] Cycloaddition Reactions via Halogen Bonding Interactions, at New York, United States, June 18, 2019.

  • R.H. Groeneman, M.A. Sinnwell, and L.R. MacGillivray, Cross-Photoreactions Utilizing Polyfluorophenyl-Phenyl Interactions, at Stellenbosch, South Africa, April 6, 2017.

  • R.H. Groeneman, E.W. Reinheimer, E. Elacqua, and L.R. MacGillivray, Dynamic Disorder of Olefins in Photoreactive Co-crystals at Oxford, England, August 7, 2013.

-Gordon Research Conference - Crystal Engineering

  • R.H. Groeneman, M.A. Sinnwell, L.R. MacGillivray, A Series of Cross-Photoreactions Utilizing Polyfluorophenyl-Phenyl Interactions in the Organic Solid State at Newry, Maine, June 25, 2018. 
  • R.H. Groeneman, Varying the Regiochemistry of a [2+2] Cycloaddition Reaction in the Organic Solid State by using Isosteric Resorcinols at Stowe, Vermont, June 28, 2016.
  • R.H. Groeneman, D.P. Ericson, M.A. Sinnwell, and L.R. MacGillivray, Supramolecular Protecting Group Strategies Applied to [2+2] Photocycloadditions Conducted in the Solid State at Waterville Valley, New Hampshire, June 2, 2014.

-Crystal Engineering and Emerging Materials Workshop of Ontario and Quebec

  • R.H. Groeneman, S.J. Kruse, and Eric Bosch, Organizing the Organic Solid State to Achieve [2 + 2] Cycloaddition Reactions via Halogen Bonding Interactions, May 30, 2020.

-National Meeting of the American Chemical Society

  • R.H. Groeneman and K.A. Kummer, Overcoming static disorder within photoreactive co-crystals by vortex grinding, 249th at Denver, March 23, 2015.
  • R.H. Groeneman, K.A. Kummer, E.W. Reinheimer, K.M. Hutchins, and L.R. MacGillivray, Structure and Dynamic Disorder of Organic Co-crystals Containing Azobenzene Derivatives, 247th at Dallas, March 19, 2014.

-Canadian Chemistry Conference

  • R.H. Groeneman, Supramolecular Protecting Group Strategies to Achieve a Series of Solid-State Photoreactions 100th at Toronto, May 30, 2017. 

  • R.H. Groeneman, Utilizing Arene-Arene Interactions and Non-conventional Hydrogen Bonds to Produce Photoreactive Solids, 99th at Halifax Nova Scotia, June 8, 2016. 

-National Meeting of the American Crystallographic Association

  • E.W. Reinheimer, L.R. MacGillivray, K.M. Hutchins and R.H. Groeneman, Using Template-Directed Co-Crystallization to Facilitate Dynamic Molecular Motion and Thermal Expansion in the Organic Solid State, at Philadelphia, July 27, 2015.
  • E.W. Reinheimer, S. Fisher, and R.H. Groeneman, Non-covalent Interactions within Complexes Containing Trimeric Perfluoro-ortho-phenylenemercury, at Philadelphia, July 27, 2015.
  • E.W. Reinheimer, D.P. Ericson, Z.P. Zurfluh-Cunningham, R.H. Groeneman, and L.R. MacGillivray, The Effect of Template Switching on the Stereochemical Selectivity of Photoactivated [2+2] Cycloaddition Reactions, at Albuquerque, May 27, 2014.

-Regional Meeting of the American Chemical Society

  • R.H. Groeneman, Incorporating organic functionality within photoreactive olefins that undergo [2+2] cycloaddition reactions within solids, 49th Midwest at Columbia, November 14, 2014.
  • H.R. Krueger, Jr., R.H. Groeneman, E.W. Reinheimer, Crystal structures based upon C-H∙∙∙N hydrogen bonding: A crystallographic and computational study, 49th Midwest at Columbia, November 14, 2014.

-Midwest Organic Solid State Chemistry Symposium

  • E.W. Reinheimer, J. Clay, and R.H. Groeneman, Urea and Thiourea Directed [2+2] Cycloaddition Reactions in the Organic Solid State, 24th at Iowa City, Iowa, June 13, 2014.