James R. Keeffe

James R. Keeffe

Professor Emeritus, deceased
At SF State since 1965


B.A. (1959), UC Santa Barbara, Chemistry
Ph.D. (1964) Univ. of Washington, Organic Chemistry

Research Interests

Computational studies applied to problems in Physical Organic Chemistry

Selected Publications

Clarke, J.; Fowler, P. W.; Gronert, S.; Keefe, J.R.  “Effect of Ring Size and Migratory Groups on [1,n] Suprafacial Shift Reactions. Confirmation of Aromatic and Antiaromatic Transition- State Character by Ring-Current Analysis”, J. Org. Chem. 2016, 81, 8777-8788.

abstract on sigmatropic shifts

I. Erden, S. Gronert, J. R. Keeffe, J. Ma, N. Ocal. C. Gärtner, L. Soukup, “Effect of Allylic Groups on SN2 Reactivity”, J. Org. Chem. 2014, 79, 6410-6418.

abstract benzyl and allyl structure

Bowler, J. T.; Wong, F. M.; Gronert, S.; Keeffe, J. R.; Wu, W., “Reactivity in the Nucleophilic Aromatic Substitution Reactions of Pyridinium  Ions”, Org. Biomol. Chem. 2014, 12, 6175-6180.

S. Gronert, J. R. Keeffe, and R. A. More O’Ferrall, “Carbene Stability”, Contemporary Carbene Chemistry”, R. A. Moss and M. P Doyle, Eds., Vol 7 in Reactive Intermediates in Chemistry and Biology series, Steven Rokita, series editor, Wiley, New York, 2014, chapter 1.

S. Gronert and J. R. Keeffe, “Calculated Stabilities and Structures for Carbocations and Singlet Carbenes Bearing Electron-withdrawing Groups”, J. Phys. Org. Chem. 2013, 26, 1023-1031.

N. A. Senger, Bo Bo,. Q. Cheng, J. R. Keeffe,, S. Gronert, W. Wu, “The Element Effect Revisited: Factors Determining Leaving Group Ability in Activated Nucleophilic Aromatic Substitution Reactions”, J. Org, Chem. 2012, 77, 9535-9540.

J. S. Kudavalli, S. N. Rao, D. E. Bean, N. D. Sharma, D. R. Boyd, P. W. Fowler, S Gronert, S. C. L. Kamerlin, J. R. Keeffe, R. A. More O’Ferrall, “Base-Catalyzed Dehydration of 3-Substituted Benzene cis-1,2-Dihydrodiols: Stabilization of a Cyclohexadienide Anion Intermediate by Negative Aromatic Hyperconjugation”, J. Am. Chem. Soc. 2012, 134, 14056-14069.

D. A. Lawlor, D. E. Bean, P. W. Fowler, J. R. Keeffe, J. S. Kudavalli, R. A. More O’Ferrall, and S. N. Rao, “Hyperaromatic Stabilization of Arenium Ions: Cyclohexa- and Cycloheptadienyl Cations – Experimental and Calculated Stabilities and Ring Currents”, J. Am. Chem. Soc. 2011, 133, 19729-19742.

S. Gronert, J. R. Keeffe, and R. A. More O’Ferrall, “Stabilities of Carbenes:  Independent Measures for Singlets and Triplets”, J. Am. Chem. Soc. 2011, 133, 3381-3389.

J. S. Kudavalli, D. R. Boyd, D. Coyne, J. R. Keeffe, D. A. Lawlor, A. C. MacCormac, R. A. More O’Ferrall, S. N. Rao, and N. D. Sharma, “Hyperaromatic Stabilization of Arenium Ions”, Org. Lett. 2010, 12, 5550-5553.

S. Gronert, J. R. Keeffe, and R. A. More O’Ferrall, “Correlations between Carbene and Carbenium Stability: Ab Initio Calculations on Substituted Phenylcarbenes, Nonbenzenoid Arylcarbenes, Heteroatom-Substituted Carbenes, and the Corresponding Carbocations and Hydrogenation Products”, J. Org. Chem. 2009, 74, 5250-5259.

J. R. Keeffe and R. A. More O’Ferrall, “The Protonation of Carbenes: Structural Effects on the -Proton Acidity of Carbocations”, Arkivoc 2008, 183-204.

S. Gronert and J. R. Keeffe, “The Protonation of Allene and Some Heteroallenes, a Computational Study”, J. Org. Chem. 2007, 72, 6343-6352).

S. Gronert and J. R. Keeffe, “Primary Semiclassical Kinetic Hydrogen Isotope Effects in Identity Carbon-to-Carbon Proton and Hydride Transfer Reactions, An ab initio and DFT Computational Study”, J. Org. Chem. 2006, 71, 5959-5968.