Professor William Karney

William Karney


Full-Time Faculty


William Karney received his BA from Haverford College and his PhD in organic chemistry from the University of California, Los Angeles. Prior to his position at USF he did postdoctoral work at the University of Washington and the University of California, Berkeley.

At USF, William teaches organic chemistry and environmental chemistry. His research, performed in collaboration with Professor Claire Castro, involves the use of computational chemistry to understand the structures, energetics, and properties of organic compounds and the mechanisms of organic reactions. Recent projects include the elucidation of mechanisms for dynamic processes in annulenes and the high-temperature rearrangements of polycyclic aromatic hydrocarbons. Current work focuses on the electronic properties of nitrenes and the contribution of heavy-atom tunneling to organic reactions.

Research Areas

  • Physical organic chemistry
  • Tunneling in organic reactions
  • Hydrocarbon reaction mechanisms


  • University of California, Los Angeles, PhD in Chemistry, 1994
  • Haverford College, BA in Chemistry, 1986

Selected Publications

  • [USF Undergraduate students in bold]
  • Castro, C.; Karney, W. L.; "Heavy-Atom Tunneling in Organic Reactions," Angew. Chem. Int. Ed. 2020, 59, 8355-8366. (Minireview)
  • 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.
  • C. S. MichelP. P. LampkinJ. Z. ShezafJ. F. Moll, C. Castro,* W. L. Karney,* "Tunneling By 16 Carbons: Planar Bond Shifting in [16]Annulene," J. Am. Chem. Soc. 2019141, 5286-5293. 
  • S. Luo, A. J. Kuhn, I. Castano, C. Castro, and W. L. Karney,* "Hydrogen Shifts in Aryl Radicals and Diradicals: The Role of m-Benzynes," J. Org. Chem. 2018, 83, 314-322.
  • S. K. Sarkar, O. Osisioma, W. L. Karney, M. Abe, and A. D. Gudmundsdottir,* "Using Molecular Architecture to Control the Reactivity of Triplet Vinylnitrene," J. Am. Chem. Soc. 2016, 138, 14905-14914.
  • E. E. Irace, E. Brayfindley, G. A. Vinnacombe, C. Castro,* and W. L. Karney,* "Stone–Wales Rearrangements in Hydrocarbons: From Planar to Bowl-Shaped Substrates," J. Org. Chem. 2015, 80, 11718-11725.
  • Brayfindley, E.; Irace, E. E.; Castro, C.; Karney, W. L. J. Org. Chem. 2015, 80, 3825-3831. DOI:  10.1021/acs.joc.5b00066. "Stone—Wales Rearrangements in Polycyclic Aromatic Hydrocarbons: A Computational Study.
  • Santander, M. V.; Pastor, M. B.; Nelson, J. N.; Castro, C.; Karney, W. L., J. Org. Chem. 2013, 78, 2033–2039. DOI: 10.1021/jo302072p. "Hückel and Möbius Bond–shifting Routes to Configuration Change in Dehydro[4n+2]annulenes."
  • Pastor, M.B.; Kuhn, A.J.; Nguyen, P.T.; Santander, M.V.; Castro, C.; Karney, W.L.,J. Phys. Org. Chem2013, 26, 750–754.  DOI:  10.1002/poc.3126. "Hydrogen Shifts and Benzene Ring Contractions in Phenylenes."
  • Castro, C.; Karney, W. L., J. Phys. Org. Chem. 2012, 25, 612-619. "Mechanisms and Möbius Strips: Understanding Dynamic Processes in Annulenes."
  • Januar, L. A.; Huynh, V.; Wood, T. S.; Castro, C.; Karney, W. L., J. Org. Chem. 2011, 76, 403–407. "Dehydro[12]annulenes: Structures, Energetics, and Dynamic Processes."
  • Okoronkwo, T.; Nguyen, P. T.; Castro, C.; Karney, W. L., Org. Lett. 2010, 12, 972–975. "[14]Annulene: Cis/trans Isomerization via Two–twist and Nondegenerate Planar Bond Shifting, and Möbius Conformational Minima."
  • Dosa, P. I.; Gu, Z.; Hager, D.; Karney, W. L.; Vollhardt, K. P. C., Chem. Commun. 2009, 1967–1969. "Flash–Vacuum–Pyrolytic Reorganization of Angular [4]Phenylene."
  • Castro, C.; Karney, W. L.; Noey, E.; Vollhardt, K. P. C., Org. Lett. 2008, 10, 1287–1290. "Competing Isomerizations of [12]Annulenes: Diels–Alder Reaction versus Electrocyclization."
  • Moll, J. F.; Pemberton, R. P.; Gutierrez, M. G.; Castro, C.; Karney, W. L., J. Am. Chem. Soc. 2007, 129, 274–275. "Configuration Change in [14]Annulene Requires Möbius Antiaromatic Bond Shifting."
  • Castro, C.; Karney, W. L.; Valencia, M. A.; Vu, C. M. H.; Pemberton, R. P., J. Am. Chem. Soc. 2005, 127, 9704–9705. "Möbius Aromaticity in [12]Annulene: Cis–Trans Isomerization via Twist–Coupled Bond Shifting."
  • Castro, C.; Isborn, C. M.; Karney, W. L.; Mauksch, M.; Schleyer, P. v. R., Org. Lett. 2002, 4, 3431–3434. "Aromaticity with a Twist: Möbius [4n]Annulenes."
  • Karney, W. L.; Borden, W. T., J. Am. Chem. Soc. 1997, 119, 1378–1387. "Ab Initio Study of the Ring Expansion of Phenylnitrene and Comparison with the Ring Expansion of Phenylcarbene."