52.      Sun, J.; Decato, D.A.; Bryantsev, V.S.; John, E.A.; Berryman, O. B.* The Interplay Between Hydrogen and Halogen Bonding: Substituent Effects and their Role in the Hydrogen Bond Enhanced Halogen Bond." Chemical Science, 2023, 14, 8924-8935. https://doi.org/10.1039/D3SC02348F

51.      Decato, D. A.*; Janke, M.†; Berryman, O. B.* “Conformational Polymorphism of 3-(azidomethyl)benzoic acid.” Acta Crystallographica Section C. 2023, 79, 344-352.

-† Denotes high school teacher co-author

50.      Decato, D. A.; Sun J.; Boller, M. R.†; Berryman, O. B.* “Pushing the Limits of the Hydrogen Bond Enhanced Halogen Bond—the Case of the C-H Hydrogen Bond.” Chemical Science, 2022, 13, 11156–11162. https://pubs.rsc.org/en/content/articlelanding/2022/SC/D2SC03792K

49.      Riel, A. M. S.; Decato, D. A.; Sun J.; Berryman, O. B.* “Halogen Bonding Organocatalysis Enhanced Through Intramolecular Hydrogen Bonds.” Chemical Communications, 2022, 58, 1378–1381. https://pubs.rsc.org/en/content/articlelanding/2022/CC/D1CC05475A

48.      Lindbald, S.; Sethio, D.; Berryman, O. B.*; Erdélyi, M.* "Modulating Photoswitch Performance with Halogen, Coordinative and Hydrogen Bonding: A Comparison of Relative Bond Strengths." Chemical Communications 2021, 57, 6261-6263. https://pubs.rsc.org/en/content/articlelanding/2021/cc/d1cc01827b#!divAbstract              

47.      Decato, D. A.; Riel, A. M. S.; May J. H.†; Bryantsev, V. S.; Berryman, O. B.* "Theoretical, Solid-State and Solution Quantification of the Hydrogen Bond Enhanced Halogen Bond." Angewandte Chemie, International Edition 2021, 60, 3685-3692. https://onlinelibrary.wiley.com/doi/full/10.1002/ange.202012262

                                          -† Denotes undergraduate co-author

46.      Turunen, L.; Németh, F. B.; Decato, D. A.; Pápai, P. I.; Berryman, O. B.*; Erdélyi, M.* "Halogen Bonds of Iodonium Ions: A World Dissimilar to Silver Coordination." Bulletin of the Chemical Society of Japan 2020, 94. 191-196. https://doi.org/10.1246/bcsj.20200274

45.      John, E. A.‡; Massena, C. J.‡; Berryman, O. B.* "Helical Anion Foldamers in Solution." Chemical Reviews 2020, 120, 5, 2783-2810. https://doi.org/10.1021/acs.chemrev.9b00583

- ‡ Both authors contributed equally

44.      Riel, A. M. S.; Huynh, H. T.; Jeannin, O.; Berryman, O. B.; Fourmigue, M.* “Organic Selenocyanates as Halide Receptors: From Chelation to One-Dimensional Systems.” Crystal Growth & Design 2019, 19, 1418-1425. https://doi.org/10.1021/acs.cgd.8b01864

43.      Riel, A. M. S.; Jeannin, O.; Berryman, O. B.; Fourmigue, M.* “Co-crystals of an Organic Triselenocyanate with Ditopic Lewis Bases: Recurrent Chalcogen Bond Interactions Motifs.” Acta Crystallographica Section B 2019, B75, 34-38. https://doi.org/10.1107/S2052520618017778

42.      Decato, D. A.; Riel, A. M. S.; Berryman, O. B.* "Anion Influence on the Packing of 1,3-Bis(4-Ethynyl-3-Iodopyridinium)-Benzene Halogen Bond Receptors." Crystals 2019, 9, 522-536. https://doi.org/10.3390/cryst9100522

41.      Riel, A. M. S.; Rowe, R. K.; Ho, E. N.; Carlsson, A.-C. C.; Rappé, A. K.; Berryman, O. B.*; Ho, P. S.* "Hydrogen Bond Enhanced Halogen Bonds: A Synergistic Interaction in Chemistry and Biochemistry." Accounts of Chemical Research 2019, 52, 2870–2880. https://doi.org/10.1021/acs.accounts.9b00189

40.      Decato, D. A.; Berryman, O. B.* "Structural and Computational Characterization of a Bridging Zwitterionic-Amidoxime Uranyl Complex." Organic Chemistry Frontiers, 2019, 6, 1038-1043, 2019. https://doi.org/10.1039/C9QO00267G

39.      Massena, C. J., Decato, D. A., Berryman, O. B.* “A Long-Lived Halogen-Bonding Anion Triple Helicate Accomodates Rapid Guest Exchange.” Angewandte Chemie, International Edition, 2018, 57, 16109-16113. https://doi.org/10.1002/anie.201810415           

38.      Riel, A. M. S.‡; Decato, D. A.‡; Sun J.; Massena, C. J.; Jessop, M. J.†; Berryman, O. B.* “The Intramolecular Hydrogen Bonded–Halogen Bond: A New Strategy for Preorganization and Enhanced Binding.” Chemical Science, 2018, 9, 5828–5836. https://doi.org/10.1039/C8SC01973H

-† Denotes undergraduate co-author    ‡ Both authors contributed equally

37.      Wageling, N. B.; Decato, D. A.; Berryman, O. B.* "Steric Effects of pH Switchable, Substituted (2-pyridinium)urea Organocatalysts: a Solution and Solid Phase Study." Supramolecular Chemistry, 2018, 30, 1004–1010.  https://doi.org/10.1080/10610278.2015.1118101

36.      Sun, J.; Riel A. M. S.; Berryman, O. B. * “Solvatochromism and Fluorescence Response of a Halogen Bonding Anion Receptor.” New Journal of Chemistry, 2018, 42, 10489–10492. https://doi.org/10.1039/C8NJ00558C

- Invited contribution to thematic issue on halogen bonding

35. Riel, A. M. S.; Jessop, M. J.†; Decato, D. A.; Massena, C. J.; Nascimento, V. R.†; Berryman, O. B.* ”Experimental Investigation of Halogen-Bond Hard-Soft Acid Base Complementarity.” Acta Crystallographica Section B, 2017, B73, 203-209. https://doi.org/10.1107/S2052520617001809

- Invited contribution to thematic issue on halogen bonding       -† Denotes undergraduate co-author

34.  Massena, C. J.; Wageling, N. B.; Decato, D. A.; Rodriguez, E. M.†; Berryman, O. B.* “A Halogen Bond Induced Triple Helicate Encapsulates Iodide.” Angewandte Chemie International Edition 2016, 55, 12398-12402. https://doi.org/10.1002/anie.201605440

- Cover art and UM press release, featured by NSF EPSCoR/IDeA Foundation, SciShow, Montana Associated Technology Rountables, Montanan Magazine, UM President’s Report, UM We Are Montana tour, highlighted in Atlas of Science      -† Denotes undergraduate co-author

33. Riel, A. M. S.; Decato, D. A.; Berryman, O. B.* “Protonation and Alkylation Induced Multidentate C–H•••Anion Binding to Perrhenate.” Crystal Growth and Design, 2016, 16, 974-980. https://doi.org/10.1021/acs.cgd.5b01524

32. Wageling, N. B.‡; Neuhaus, G. F.‡†; Rose, A. M.; Decato, D. A.; Berryman, O. B.* “Advantages of Organic Halogen Bonding for Halide Recognition.” Supramolecular Chemistry, 2016, 28, 665-672. https://doi.org/10.1080/10610278.2015.1118101

-† Denotes undergraduate co-author     ‡ Both authors contributed equally

31. Massena, C. J.; Riel, A. M. S.; Neuhaus, G. F.†; Decato, D. A.; Berryman, O. B.* “Solution and Solid-Phase Halogen and C-H Hydrogen Bonding to Perrhenate.” Chemical Communications, 2015, 51, 1417-1420. https://doi.org/10.1039/C4CC09242B

                          -† Denotes undergraduate co-author

30. Decato, D. A.; Berryman, O. B.* “Crystal Structure of [1,1':3',1''-Terphenyl]-2',3,3''-Tricarboxylic Acid.” Acta Crystallographica Section E, 2015, E71, o667-o668. https://doi.org/10.1107/S2056989015015029

29. Tresca, B. W.; Berryman, O. B.; Zakharov, L. N.; Johnson, D. W.; Haley, M. M. “Anion-Directed Self-Assembly of a 2,6-bis(2-Anilinoethynyl)pyridine Bis(amide) scaffold.” Supramolecular Chemistry, 2016, 28, 37-44. https://doi.org/10.1080/10610278.2015.1072199 (invited for special issue in honor of Jonathan L. Sessler)

28. Berryman, O. B.; Johnson, C. A.; Vonnegut, C. L.; Fajardo, K. A.; Zakharov, L. N.; Johnson, D. W.; Haley, M. M. “Solid-State Examination of Conformationally Diverse Sulfonamide Receptors Based on Bis(2-anilinoethynyl)pyridine, -Bipyridine, and -Thiophene.” Crystal Growth and Design, 2015, 15, 1502-1511. https://doi.org/10.1021/cg5018856

27. Sather, A. C.; Berryman, O. B.; Rebek, J. Jr. “Selective Recognition and Extraction of the Uranyl Ion from Aqueous Solutions with a Recyclable Chelating Resin.” Chemical Science, 2013, 4, 3601-3605. https://doi.org/10.1039/C3SC51507A

26. Sather, A. C.; Berryman, O. B.; Moore, C. E.; Rebek, J. Jr. “Uranyl Ion Coordination with Rigid Aromatic Carboxylates and Structural Characterization of their Complexes.” Chemical Communications, 2013, 49, 6379-6381. https://doi.org/10.1039/C3CC43358G

25. Collins, M. S.; Carnes, M. E.; Sather, A. C.; Berryman, O. B.; Zakharov, L. N.; Teat, S. J.; Johnson, D. W. “Pnictogen-Directed Synthesis of Discrete Disulfide Macrocycles.” Chemical Communications, 2013, 49, 6599-6601. https://doi.org/10.1039/C3CC43524E

24. Sather, A. C.; Berryman, O. B.; Rebek, J. Jr. “Synthesis of Fused Indazole Ring Systems and Application to Nigeglanine Hydrobromide.” Organic Letters, 2012, 14, 1600-1603. https://doi.org/10.1021/ol300303s

23. Berryman, O. B.; Sather, A. C.; Lledo, A.; Rebek, J. Jr. “Switchable Catalysis with a Light Responsive Cavitand.” Angewandte Chemie International Edition, 2011, 50, 9400-9403. https://doi.org/10.1002/anie.201105374

                          - Editor designated “hot paper” for importance in a rapidly evolving field of high interest.

22. Berryman, O. B.; Sather, A. C.; Rebek, J. Jr. “A Deep Cavitand with a Fluorescent Wall Functions as an Ion Sensor.” Organic Letters, 2011, 13, 5232-5235. https://doi.org/10.1021/ol2021127

21. Berryman, O. B.; Dube, H.; Rebek, J. Jr. “Photophysics Applied to Cavitands and Capsules.” Israel Journal of Chemistry, 2011, 51, 700-709. https://doi.org/10.1002/ijch.201100055

                          - Invited review article

20. Fontenot, S. A.; Cangelosi, V. M.; Pitt, M. A. W.; Sather, A. C.†; Zakharov, L. N.; Berryman, O. B.; Johnson, D. W. “Design, Synthesis and Characterization of Self-Assembled As₂L₃ and Sb₂L₃ Cryptands.” Dalton Transactions, 2011, 40, 12125-12131. https://doi.org/10.1039/C1DT10817D

19. Gavette, J. V.; Lara, J.; Berryman, O. B.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Lithium Cation Enhances Anion Binding in a Tripodal Phosphine Oxide-Based Ditopic Receptor.” Chemical Communications, 2011, 47, 7653-7655. https://doi.org/10.1039/C1DT10817D

18. Carroll, C. N.; Coombs, B. A.; McClintock, S. P.; Johnson, C. A.; Berryman, O. B.; Johnson, D. W.; Haley, M. M. “Anion-Dependent Fluorescence in Bis(anilinoethynyl)pyridine Derivatives: Switchable ON-OFF and OFF-ON responses.” Chemical Communications, 2011, 47, 5539-5541. https://doi.org/10.1039/C1CC10947B

17.  Berryman, O. B.; Sather, A. C.; Rebek, J. Jr. “A Light Controlled Cavitand Wall Regulates Guest Binding.” Chemical Communications, 2011, 47, 656-658. https://doi.org/10.1039/C0CC03865B

16.  Sather, A. C.; Berryman, O. B.; Ajami, D.; Rebek, J. Jr. “Reactivity of N-nitrosoamides in Confined Spaces.” Tetrahedron Letters, 2011, 52, 2100-2103. http://doi.org/10.1016/j.tetlet.2010.11.030

15.  Sather, A. C.; Berryman, O. B.; Rebek, J. Jr. “Selective Recognition and Extraction of the Uranyl Ion.” Journal of the American Chemical Society, 2010, 132, 13572-13574. https://doi.org/10.1021/ja1035607

14. Beer, S.‡; Berryman, O. B.‡; Ajami, D.; Rebek, J. Jr. “Encapsulation of the Uranyl Dication.” Chemical Science, 2010, 1, 43-47. https://doi.org/10.1039/C0SC00116C

-‡ Both authors contributed equally. Highlighted in RSC press release, UK’s Daily Telegraph, MSN news, Yahoo News and AOL news. Cover art.

13. Restorp, P.; Berryman, O. B.; Sather, A. C.; Ajami, D.; Rebek, J. Jr. “A Synthetic Receptor for Hydrogen Bonding to Fluorines of Trifluoroborates.” Chemical Communications, 2009, 5692-5694. https://doi.org/10.1039/B914171E

12. Johnson, C. A.; Berryman, O. B.; Sather A. C.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Anion Binding Induces Helicity in a Hydrogen Bonding Receptor: Crystal Structure of a 2,6-Bis(anilinoethynyl)pyridinium Chloride.” Crystal Growth and Design, 2009, 9, 4247-4249. https://doi.org/10.1021/cg900674p

11.  Berryman, O. B.; Johnson, D. W. “Experimental Evidence of Interactions Between Anions and Electron-Deficient Aromatic Rings.” Chemical Communications, 2009, 3143-3153. https://doi.org/10.1039/B823236A

                          - Invited feature article and cover art.

10.  Carroll, C. N.; Berryman, O. B.; Johnson, C. A.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Protonation Activates Anion Binding and Alters Binding Selectivity in New Inherently Fluorescent 2,6-bis(2-anilinoethynyl)pyridine Bisureas.” Chemical Communications, 2009, 2520-2522. https://doi.org/10.1039/B901643K

 9.   Berryman, O. B.; Sather, A. C.; Meisner, J. S.; Hay, B. P.; Johnson, D. W. “Solution Phase Measurement of Both Weak Sigma Complexes and C-H•••X^– Hydrogen Bonding Interactions in a Synthetic Receptor.” Journal of the American Chemical Society, 2008, 130, 10895-10897. https://doi.org/10.1021/ja8035652

8.    Berryman, O. B.; Johnson, C. A.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Water and Hydrogen Halides Serve the Same Structural Role in a Series of 2+2 Hydrogen-Bonded Dimers Based on 2,6-bis(2-anilinoethynyl)pyridine Sulfonamide Receptors.” Angewandte Chemie International Edition, 2008, 47, 117-120. https://doi.org/10.1002/anie.200703971

 7.   Shultz, G. V.; Berryman, O. B.; Zakharov, L. N.; Tyler, D. R. “Preparation of Photodegradable Polymers Containing Metal-Metal Bonds Using ADMET.” Journal of Inorganic and Organometallic Polymers and Materials, 2008, 18, 149-154. https://doi.org/10.1007/s10904-007-9174-8

 6.   Berryman, O. B.; Bryantsev, V. S.; Stay, D. P.; Johnson, D. W.; Hay, B. P. “Structural Criteria for the Design of Anion Receptors: the Interaction of Halides with Electron-Deficient Arenes.” Journal of the American Chemical Society, 2007, 129, 48-58. https://doi.org/10.1021/ja063460m

- UO Press release – December 2006, cited 268 times, Web of Science highly cited paper.

 5.   Meisner, J. S.; Berryman, O. B.; Zakharov, L. N.; Johnson, D. W. “Methyl 4-bromo-3,5-dinitrobenzoate.” Acta Crystallographica Section E, 2007, 63, o2466. https://doi.org/10.1107/S1600536807017874

 4.   Cangelosi, V. A.; Sather, A. C.; Zakharov, L. N.; Berryman, O. B.; Johnson, D. W. “Diastereoselectivity in the Self-Assembly of As₂L₂Cl₂ Macrocycles is Directed by the As-π Interaction.” Inorganic Chemistry, 2007, 46, 9278-9284. https://doi.org/10.1021/ic701290h

 3.   Berryman, O. B.; Hof, F.; Hynes, M. J.; Johnson, D. W. "Anion-π Interaction Augments Halide Binding in Solution." Chemical Communications, 2006, 506-508. https://doi.org/10.1039/B511570A

 2.   Johnson, C. A.; Baker, B. A.; Berryman, O. B.; Zakharov, L. N.; O'Connor, M. J.; Haley, M. M. "Synthesis and Characterization of Pyridine- and Thiophene-Based Platinacyclyne." Journal of Organometallic Chemistry, 2006, 691, 413-421. http://doi.org/10.1016/j.jorganchem.2005.09.008

 1.   Vickaryous, W. J.; Healey, E. R.; Berryman, O. B.; Johnson, D. W. "Synthesis and Characterization of Two Isomeric, Self-Assembled Arsenic-Thiolate Macrocycles." Inorganic Chemistry, 2005. 44, 9247-9252. https://doi.org/10.1021/ic050954w

Book Chapters

1. Decato, D. A.; John, E. A. Berryman, O. B.*; “Halogen Bonding: An Introduction.” In: Huber, S. M., Ed Halogen Bonding in Solution; Wiley-VCH Publishers. 2021, vol. 1, pp 1-41. https://doi.org/10.1002/9783527825738.ch1

 

B.    Riel, A. M. S.; Wageling, N. B.; Decato, D. A.; Berryman, O. B.* “Anion-Arene Interactions and the Anion-π Phenomenon.” In: Atwood, J. L., (ed.) Comprehensive Supramolecular Chemistry II, 2017, vol. 1, pp. 149-184. Oxford: Elsevier. https://doi.org/10.1016/B978-0-12-409547-2.12484-9

 

C.    Decato, D. A.; Berryman, O. B.*; “Simultaneous Halogen and Hydrogen Bonding to Carbonyl and Thiocarbonyl Functionality” in Aspects of Multi-component Crystals: Synthesis, Concepts and Function, 2018, vol. 1, pp272-288. Tiekink, E. R. T., Eds; De Gruyter Publishers. https://doi.org/10.1515/9783110464955-012

 

D.   Rather Healey, E.; Vickaryous, W. J.; Berryman, O. B.; Johnson, D. W. “Self-Assembled Supramolecular Main Group Coordination Complexes” in BOTTOM-UP NANOFABRICATION: Supramolecules, Self-Assemblies, and Organized Films.” Ariga, K., Nalwa, H. S., Eds.; American Scientific Publishers: Stevenson Ranch, 2007.

PATENTS

I.     Berryman, O. B.; Palmer Christopher; “Stationary Phase Chromatography Methods and Compounds.” Filed February 7, 2022. Application No. 63307258.

II.    Lohrman, J.; Riel A. M. S.; Decato, D. A.; Haley, M.; Johnson, D. W.; Berryman, O. B.; “Fluorescent Halogen Bonding Arylethynyl Scaffolds for Anion Recognition.” filed May 1, 2019. U.S. Patent No. 16/401,037.

III.   Berryman, O. B.; Massena, C. J. “A Halogen-Bond-Induced Triple Helicate Encapsulates Iodide.” Serial No. 62/362,226, filed July 14, 2016.

IV. Haley, M. M.; Johnson, D. W.; Berryman, O. B.; Johnson, C. A.; Stimpson, C. A. “Process for Preparation of Tunable Phenylacetylene Host Compounds for Ligand Binding.” U.S. Pat. Appl. US 2008167472, 2008, 21.

V. Rebek, J. Jr.; Berryman, O. B.; Sather, A. C. “Methods and Compositions for Chelating Metals in Aqueous Solutions.” US Pat. Application # 61/217,078, 2009.