Castro / Karney Research Publications

(USF Undergraduate students underlined)

  1. W. L. Karney,* E. R. Carson, I. Jain, A. V. Nilsen, B. P. Quinn, L. Sosa, "Influence of Heavy-Atom Tunneling on Pericyclic Reactions in Biosynthesis: A Computational Study," J. Org. Chem. 2025, 90, in press.

  2. C. J. Laconsay, I. Jain, T. Schleif,* W. L. Karney,* J. I. Wu,* "Geminal Hyperconjugation as a Driving Force for C-C Bond Shortening in Heavy-Atom Tunneling," Chem. Sci. 2025, 16, in press.

  3. F. J. Wasson, A. Borah, D. Govorov, W. Dinindu Mendis, J. S. Poole, B. S. Ault, W. L. Karney, A. D. Gudmundsdottir,* "Aromaticity and Photoreactivity of 4- and 3-Nitrenopyridine 1-Oxides and Phenylnitrene," J. Phys. Org. Chem. 2025, 38, in press.

  4. C. Leung, U. M. Bashir, W. L. Karney, M. G. Swanson, H. Nikolayevskiy,* "Mechanistic Analysis of 5-Hydroxy γ-Pyrones as Michael Acceptor Prodrugs," J. Org. Chem. 2024, 89, 12432-12438.

  5. O. Osisioma, L. J. Patton, R. Merugu, D. Govorov, M. A. Milbrandt, C. Jarus, W. L. Karney, A. D. Gudmundsdottir,* "Formation of Stilbene Azo-Dimer by Direct Irradiation of p-Azidostilbene," Photochem. Photobiol. 2023, 99, 605-615.

  6. K. T. Hewa, W. Sebastien, E. M. Lemen, W. L. Karney, M. Abe, A. D. Gudmundsdottir,* "Photolysis of 3-Azido-3-phenyl-3H-isobenzofuran-1-one at Ambient and Cryogenic Temperatures," Photochem. Photobiol. 2021, 97, 1397-1406.

  7. U. Banerjee, S. K. Sarkar, J. A. Krause, W. L. Karney, M. Abe, A. D. Gudmundsdottir,* "Photoinduced α-Cleavage of 2-Azido-2-phenyl-1,3-indandione at Cryogenic Temperatures," Org. Lett. 2020, 22, 7885-7890.

  8. U. Banerjee, W. L. Karney, B. S. Ault, A. D. Gudmundsdottir,* "Photolysis of 5-Azido-3-Phenylisoxazole at Cryogenic Temperature: Formation and Direct Detection of a Nitrosoalkene," Molecules 2020, 25, 543-557.

  9. C. Castro,* W. L. Karney,* "Heavy-Atom Tunneling in Organic Reactions," Angew. Chem. Int. Ed. 2020, 59, 8355-8366.

  10. J. K. Arbitman, C. S. Michel, C. Castro,* W. L. Karney,* "Calculations Predict That Heavy-Atom Tunneling Dominates Möbius Bond Shifting in [12]- and [16]Annulene," Org. Lett. 2019, 21, 8587-8591.

  11. D. M. Gatlin, W. L. Karney, M. Abe, B. S. Ault, A. D. Gudmundsdottir,* "Formation and Reactivity of Vinylnitrenes as a Function of Ring Size," J. Org. Chem. 2019, 84, 9215-9225.

  12. C. S. Michel, P. P. Lampkin, J. Z. Shezaf, J. F. Moll, C. Castro,* W. L. Karney,* "Tunneling by 16 Carbons: Planar Bond Shifting in [16]Annulene," J. Am. Chem. Soc. 2019, 141, 5286-5293.

  13. S. Luo, A. J. Kuhn, I. Castano, C. Castro, W. L. Karney,* "Hydrogen Shifts in Aryl Radicals and Diradicals: The Role of m-Benzynes," J. Org. Chem. 2018, 83, 314-322.

  14. S. K. Sarkar, O. Osisioma, W. L. Karney, M. Abe, A. D. Gudmundsdottir,* "Using Molecular Architecture to Control the Reactivity of Triplet Vinylnitrene," J. Am. Chem. Soc. 2016, 138, 14905-14914.

  15. E. E. Irace, E. Brayfindley, G. A. Vinnacombe, C. Castro,* W. L. Karney,* "Stone-Wales Rearrangements in Hydrocarbons: From Planar to Bowl-Shaped Substrates," J. Org. Chem. 2015, 80, 11718-11725. (Invited manuscript for special issue: 50 Years and Counting: The Woodward-Hoffmann Rules in the 21st Century)

  16. E. Brayfindley, E. E. Irace, C. Castro,* W. L. Karney,* "Stone-Wales Rearrangements in Polycyclic Aromatic Hydrocarbons: A Computational Study," J. Org. Chem. 2015, 80, 3825-3831.

  17. M. B. Pastor, A. J. Kuhn, P. T. Nguyen, M. V. Santander, C. Castro,* W. L. Karney,* "Hydrogen Shifts and Benzene Ring Contractions in Phenylenes," J. Phys. Org. Chem. 2013, 26, 750-754. (Invited article for special issue on ISRIUM 2012).

  18. M. V. Santander, M. B. Pastor, J. N. Nelson, C. Castro*, W. L. Karney,* "Hückel and Möbius Bond-Shifting Routes to Configuration Change in Dehydro[4n+2]annulenes," J. Org. Chem. 2013, 78, 2033-2039 (Invited article for Howard Zimmerman Memorial Issue).

  19. C. Castro,* W. L. Karney,* "Mechanisms and Möbius Strips: Understanding Dynamic Processes in Annulenes," J. Phys. Org. Chem. 2012, 25, 612-619 (Invited mini-review with featured cover art).

  20. L. A. Januar, V. Huynh, T. S. Wood, C. Castro,* W. L. Karney,* "Dehydro[12]annulenes: Structures, Energetics, Conformational Processes, and Computed NMR Parameters," J. Org. Chem. 2011, 76, 403-407.

  21. T. Okoronkwo, P. T. Nguyen, C. Castro,* W. L. Karney,* "[14]Annulene: Cis/Trans Isomerization via Two-Twist and Nondegenerate Planar Bond Shifting and Möbius Conformational Minima," Org. Lett. 2010, 12, 972-975.

  22. P. I. Dosa, Z. Gu, D. Hager, W. L. Karney, K. P. C. Vollhardt,* "Flash-Vacuum-Pyrolytic Reorganization of Angular [4]Phenylene," Chem. Commun. 2009, 1967-1969.

  23. M. N. Braten, M. G. Gutierrez, C. Castro,* W. L, Karney,* "[12]Annulene Radical Anions Revisited: Evaluation of Structure Assignments Based on Computed Energetic and Electron Spin Resonance Data," J. Org. Chem. 2008, 73, 8745-8754.

  24. C. Castro,* W. L. Karney, E. Noey, K. P. C. Vollhardt,* "Competing Isomerizations of [12]Annulenes: Diels-Alder Reaction vs. Electrocyclization," Org. Lett. 2008, 10, 1287-1290.

  25. M. N. Braten, C. Castro,* R. Herges,* F. Köhler, W. L. Karney,* "The [12]Annulene Global Minimum," J. Org. Chem. 2008, 73, 1532-1535.

  26. J. F. Moll, R. P. Pemberton, M. G. Gutierrez, C. Castro,* W. L. Karney,* "Configuration Change in [14]Annulene Requires Möbius Antiaromatic Bond Shifting," J. Am. Chem. Soc. 2007, 129, 274-275.

  27. R. P. Pemberton, C. M. McShane, C. Castro,* W. L. Karney,* "Dynamic Processes in [16]Annulene: Möbius Bond-Shifting Routes to Configuration Change," J. Am. Chem. Soc. 2006, 128, 16692-16700.

  28. C. Castro,* W. L. Karney,* C. M. McShane, R. P. Pemberton, "[10]Annulene: Bond Shifting and Conformational Mechanisms for Automerization," J. Org. Chem. 2006, 71, 3001-3006.

  29. C. Castro,* W. L. Karney,* M. A. Valencia, C. M. H. Vu, R. P. Pemberton, "Möbius Aromaticity in [12]Annulene: Cis-Trans Isomerization via Twist-Coupled Bond Shifting," J. Am. Chem. Soc. 2005, 127, 9704-9705.

  30. C. Castro,* W. L. Karney,* C. M. H. Vu, S. E. Burkhardt, M. A. Valencia, "Computational Evaluation of the Evidence for Tri-trans-[12]Annulene," J. Org. Chem. 2005, 70, 3602-3609.

  31. C. Castro,* Z. Chen, C. S. Wannere, H. Jiao, W. L. Karney,* M. Mauksch, R. Puchta, N. J. R. van Eikema Hommes, P. v. R. Schleyer,* "Investigation of a Putative Möbius Aromatic Hydrocarbon. The Effect of Benzannelation on Möbius [4n]Annulene Aromaticity," J. Am. Chem. Soc. 2005, 127, 2425-2432.

  32. C. Castro,* C. M. Isborn, W. L. Karney,* M. Mauksch, P. v. R. Schleyer,* "Aromaticity with a Twist: Möbius [4n]Annulenes," Org. Lett. 2002, 4, 3431-3434.

  33. W. L. Karney,* C. J. Kastrup, S. P. Oldfield, and H. S. Rzepa,* "Möbius Forms of 8-π Electron Heteropines," J. Chem. Soc., Perkin Trans. 2 2002, 388-392.

  34. W. L. Karney* and W. T. Borden,* "Differences Between Phenylcarbene and Phenylnitrene and the Ring Expansions They Undergo," Advances in Carbene Chemistry, Vol. 3, U. H. Brinker, Ed.; Elsevier: Amsterdam, 2001; pp 205-251.

  35. N. P. Gritsan,* A. D. Gudmundsdóttir, D. Tigelaar, Z. Zhu, W. L. Karney,* C. M. Hadad,* and M. S. Platz,* "A Laser Flash Photolysis and Quantum Chemical Study of the Fluorinated Derivatives of Singlet Phenylnitrene," J. Am. Chem. Soc. 2001, 123, 1951-1962.

  36. N. P. Gritsan,* I. Likhotvorik, M.-L. Tsao, N. Çelebi, M. S. Platz,* W. L. Karney, C. R. Kemnitz, and W. T. Borden,* "Ring-Expansion Reaction of Cyano-Substituted Singlet Phenyl Nitrenes: Theoretical Predictions and Kinetic Results from Laser Flash Photolysis and Chemical Trapping Experiments," J. Am. Chem. Soc. 2001, 123, 1425-1433.

  37. W. T. Borden,* N. P. Gritsan,* C. M. Hadad,* W. L. Karney, C. R. Kemnitz, and M. S. Platz,* "The Interplay of Theory and Experiment in the Study of Phenylnitrene," Acc. Chem. Res. 2000, 33, 765-771.

  38. C. R. Kemnitz, G. B. Ellison, W. L. Karney, and W. T. Borden,* "CASSCF and CASPT2 Ab Initio Electronic Structure Calculations Find Singlet Methylnitrene is an Energy Minimum," J. Am. Chem. Soc. 2000, 122, 1098-1101.

  39. L. L. Stracener, R. J. Halter, R. J. McMahon,* C. Castro, W. L. Karney,* "Singlet-Triplet Energy Separation of Cyclobutylidene," J. Org. Chem. 2000, 65, 199-204.

  40. C. Castro,* C. Chen, and M. E. Jung,* "Intramolecular Glycosylation to Form 4-Methoxy-2,6-dioxopyrimidine Nucleosides via O6,5'-Cyclonucleosides," Nucleosides Nucleotides 1999, 18, 2415-2423.

  41. M. E. Jung,* C. Castro, and S. I. Khan, "Novel Lewis Acid-Catalyzed Rearrangement of a Sugar-Base Hybrid to Afford an Anhydronucleoside," Nucleosides Nucleotides 1998, 17, 2383-2387.

  42. C. Castro,* W. L. Karney,* "Incorporating Organic Name Reactions and Omitting Qualitative Analysis in an Unknown Identification Experiment," J. Chem. Educ. 1998, 75, 472-475.

  43. C. R. Kemnitz, W. L. Karney, W. T. Borden,* "Why Are Nitrenes More Stable Than Carbenes? An Ab Initio Study," J. Am. Chem. Soc. 1998, 120, 3499-3503.

  44. W. L. Karney* and W. T. Borden,* "Why Does o-Fluorine Substitution Raise the Barrier to Ring Expansion in Phenylnitrene?" J. Am. Chem. Soc. 1997, 119, 3347-3350.

  45. W. L. Karney* and W. T. Borden,* "Ab Initio Study of the Ring Expansion of Phenylnitrene and Comparison with the Ring Expansion of Phenylcarbene," J. Am. Chem. Soc. 1997, 119, 1378-1387.

  46. P. R. Schreiner,* W. L. Karney, P. v. R. Schleyer,* T. P. Hamilton, W. T. Borden,* and H. F. Schaefer III, "Carbene Rearrangements Unsurpassed: Details of the C7H6 Potential Energy Surface Revealed," J. Org. Chem. 1996, 61, 7030-7039.

  47. R. F. Gunion, W. Karney, P. G. Wenthold, W. T. Borden,* and W. C. Lineberger,* "Ultraviolet Photoelectron Spectroscopy of Some C7H7– Isomers: Quadricyclanide, Norbornadienide, Cycloheptatrienide, and 1,6-Heptadiynide," J. Am. Chem. Soc. 1996, 118, 5074-5082.

  48. M. Selke, W. L. Karney, S. I. Khan, and C. S. Foote,* "Reactions of Singlet Oxygen with Organometallic Complexes. 3. Kinetics and Scope of the Oxidative Addition Reaction of Singlet Oxygen with Iridium(I), Rhodium(I), and Platinum(II) Complexes," Inorg. Chem. 1995, 34, 5715-5720.

  49. M. Selke, C. S. Foote,* and W. L. Karney, "Reactions of Singlet Oxygen with Organometallic Complexes. 2. Formation of a Metastable Rhodium-Dioxygen Complex," Inorg. Chem. 1993, 32, 5425-5426.

  50. M. E. Jung* and C. Castro,"New Approach to the Synthesis of β-2'-Deoxyribonucleosides," J. Org. Chem. 1993, 58, 807-808.

  51. J. V. Z. Krevor, U. Simonis, A. Karson, C. Castro, and M. Aliakbar, "Determination of the Magnitude and Sign of the 2JPt-P Coupling Constants in Dinuclear Platinum(I) Phosphine Complexes by Two-Dimensional 31P NMR Spectroscopy," Inorg. Chem. 1992, 31, 312-317.

  52. K.-J. Fu, W. L. Karney, O. L. Chapman, S.-M. Huang, R. B. Kaner,* F. Diederich, K. Holczer, and R. L. Whetten,* "Giant Vibrational Resonances in A6C60 Compounds," Phys. Rev. B 1992, 46, 1937-1940.

  53. M. E. Jung,* C. Castro, and J. M. Gardiner, "Rapid Synthesis of 2',3'-Dideoxycytidine (ddC) From a Simple Achiral Precursor," Tetrahedron Lett. 1991, 32, 5717-5720.

  54. C. Castro, M. Dixon, I. Erden,* P. Ergonenc, J. R. Keeffe,* and A. Sukhovitsky, "Dye-Sensitized Photooxygenation of the Carbon-Nitrogen Double Bond," J. Org. Chem. 1989, 54, 3732-3738.