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Kendall Houk, Ph.D.

   
Saul Winstein Chair, Organic Chemistry
Lab Director, Houk Lab
Professor, Chemistry and Biochemistry, Organic Chemistry
Member, NanoElectronics, Photonics, Architectonics, NanoMechanical and Nanofluidic Systems, California NanoSystems Institute
Researcher, Chemical Biology, Organic, Theoretical Chemistry

Education:
Degrees:
Ph.D., Harvard University, 1968

Honors and Awards:
2003 Computers in Chemical and Pharmaceutical Research, ACS Award for Computers in Chemistry and Pharmaceutical Research
2002 American Academy of Arts and Sciences, American Academy of Arts and Sciences
2001 Japanese Society for the Promotion of Science, Fellow of the JSPS
2000 Technion, Israel, Lady Davis Fellow
2000 Hebrew University, Jerusalem Israel, Lise Meitner Lecturer
1999 American Chemical Society Southern California Section, Tolman Medal
1998 World Association of Theoretical Organic Chemistry, Schrodinger Medal
1993 Herbert Newby McCoy Award, UCLA
1993 University of Canterbury, Christchurch, New Zealand, Visiting Erskine Fellow
1991 James Flack Norris Award in Physical Organic Chemistry
1988 Arthur C. Cope Scholar Award
1988 Fellow of the American Association for the Advancement of Science
1983 Akron Section of the American Chemical Society Award
1982 Von Humboldt U.S. Senior Scientist Award
1978 LSU Distinguished Research Master Award
1975 - 1977 Alfred P. Sloan Foundation Research Fellowship
1972 - 1977 Camille and Henry Dreyfus Teacher-Scholar Grant

Professional Societies:
American Association for the Advancement of Science
International Society of Quantum Biology
Chemical Society of London
American Chemical Society
Inter-American Photochemical Society
2003 International Academy of Quantum Moelcular Science

Contact Information:
Email Address: houk@chem.ucla.edu
Work Email Address: houk@chem.ucla.edu
Laboratory Address: Mol Sci Bldg 5240, 5440
Work Address: Mol Sci Bldg 5505B
Laboratory: http://www.chem.ucla.edu/dept/Faculty/houk.html/
Work Phone Number: 1 (310) 206-0515
Lab Number: 1 (310) 825-0269
Fax Number: 1 (310) 206-1843
Additional Information:

K. N. Houk was born in Nashville, Tennessee in 1943. He received his A.B. (1964), M.S. (1966), and Ph.D. (1968) degrees at Harvard, working with R. A. Olofson as an undergraduate and R. B. Woodward as a graduate student in the area of experimental tests of orbital symmetry selection rules. In 1968, he joined the faculty at Louisiana State University, becoming Professor in 1976. He has also been a Visiting Professor at Princeton. In 1980, he moved to the University of Pittsburgh, and in 1986, he moved to U.C.L.A., becoming a Distinguished Professor in 1987.

He has served on the Advisory Boards of the Chemistry Division of the National Science Foundation, the Petroleum Research Fund, a variety of journals, including Accounts of Chemical Research, the Journal of the American Chemical Society, the Journal of Organic Chemistry, Chemical and Engineering News, the Journal of Computational Chemistry, Chemistry-A European Journal, and the Journal of Chemical Theory and Computation. He was a member of the NIH Medicinal Chemistry Study Section and the NRC Board of Chemical Sciences and Technology. From 1988-1990, he was Director of the Chemistry Division of the National Science Foundation. He was Chairman of the UCLA Department of Chemistry and Biochemistry from 1991-1994 and was Chair of the AAAS Chemistry Section in 2005. He is a Fellow of the American Academy of Arts and Sciences, the American Association for the Advancement of Science, and of the World Association of Theoretical and Computational Chemists (new name of WATOC). He was co-chair, with Professor Cynthia Friend of Harvard, of a NSF-NIH-DOE-sponsored Workshop on Building Strong Academic Chemistry Departments Through Gender Equity in 2006. He currently is the Director of the UCLA Chemistry-Biology Interface Training Program and Senior Editor of Accounts of Chemical Research. He is a member of the NIH SBC-A Study Section and is Chair for 2007-2008. On July 1, 2009, he becomes the Saul Winstein Chair of Organic Chemistry at UCLA

He has published more than 750 articles in refereed journals, is among the 100 most-cited chemists, and is an avid runner, biker, and swimmer.

Selected Publications:

Kersey Black, Peng Liu, Lai Xu, Charles Doubleday, and Kendall N. Houk, Dynamics, transition states, and timing of bond formation in Diels–Alder reactions, PNAS, 2012, 1-6.
Moonhee Kim, J. Nathan Hohman, Yang Cao, Kendall N. Houk, Hong Ma, Alex K.-Y. Jen, and Paul S. Weiss, Creating Favorable Geometries for Directing Organic Photoreactions in Alkanethiolate Monolayers, Science, 2011, 331 (6022), 1312-5.
Wheeler SE, Houk KN, Are anion/pi interactions actually a case of simple charge-dipole interactions?, J Phys Chem A, 2010, 114 (33), 8652-64.
Aghajan M, Jonai N, Flick K, Fu F, Luo M, Cai X, Ouni I, Pierce N, Tang X, Lomenick B, Damoiseaux R, Hao R, Del Moral PM, Verma R, Li Y, Li C, Houk KN, Jung ME, Zheng N, Huang L, Deshaies RJ, Kaiser P, Huang J, Chemical genetics screen for enhancers of rapamycin identifies a specific inhibitor of an SCF family E3 ubiquitin ligase, Nat Biotechnol, 2010, 28 (7), 738-42.
Siegel JB, Zanghellini A, Lovick HM, Kiss G, Lambert AR, St Clair JL, Gallaher JL, Hilvert D, Gelb MH, Stoddard BL, Houk KN, Michael FE, Baker D, Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction, Science, 2010, 32 (5989), 309-13.
Jones GO, Liu P, Houk KN, Buchwald SL, Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions, J Am Chem Soc, 2010, 132 (17), 6205-13.
Allemann C, Um JM, Houk KN, Computational investigations of the stereoselectivities of proline-related catalysts for aldol reactions, J Mol Catal A Chem, 2010, 324 (1-2), 31-38.
Gül S, Schoenebeck F, Aviyente V, Houk KN, Computational study of factors controlling the boat and chair transition states of Ireland-Claisen rearrangements, J Org Chem, 2010, 75 (6), 2115-8.
Xu L, Doubleday CE, Houk KN, Dynamics of 1,3-dipolar cycloadditions: energy partitioning of reactants and quantitation of synchronicity, J Am Chem Soc, 2010, 132 (9), 3029-37.
Liu P, Sirois LE, Cheong PH, Yu ZX, Hartung IV, Rieck H, Wender PA, Houk KN, Electronic and steric control of regioselectivities in Rh(I)-catalyzed (5 + 2) cycloadditions: experiment and theory, J Am Chem Soc, 2010, 132 (29), 10127-35.
Kiss G, Röthlisberger D, Baker D, Houk KN, Evaluation and ranking of enzyme designs, Protein Sci, 2010, 19 (9), 1760-73.
Wheeler SE, Houk KN, Integration Grid Errors for Meta-GGA-Predicted Reaction Energies: Origin of Grid Errors for the M06 Suite of Functionals, J Chem Theory Comput, 2010, 6 (2), 395-404.
Schoenebeck F, Houk KN, Ligand-controlled regioselectivity in palladium-catalyzed cross coupling reactions, J Am Chem Soc, 2010, 132 (8), 2496-7.
Um JM, Gutierrez O, Schoenebeck F, Houk KN, MacMillan DW, Nature of intermediates in organo-SOMO catalysis of alpha-arylation of aldehydes, J Am Chem Soc, 2010, 132 (17), 6001-5.
Paton RS, Mackey JL, Kim WH, Lee JH, Danishefsky SJ, Houk KN, Origins of stereoselectivity in the trans Diels-Alder paradigm, J Am Chem Soc, 2010, 132 (27), 9335-40.
St-Cyr DJ, Morin MS, Bélanger-Gariépy F, Arndtsen BA, Krenske EH, Houk KN, Phospha-Münchnones: electronic structures and 1,3-dipolar cycloadditions, J Org Chem, 2010, 75 (12), 4261-73.
Wheeler SE, McNeil AJ, Müller P, Swager TM, Houk KN, Probing substituent effects in aryl-aryl interactions using stereoselective Diels-Alder cycloadditions, J Am Chem Soc, 2010, 132 (10), 3304-11.
Chen HY, Hou J, Hayden AE, Yang H, Houk KN, Yang Y, Silicon atom substitution enhances interchain packing in a thiophene-based polymer system, Adv Mater, 2010, 22 (3), 371-5.
Jung ME, Zhang TH, Lui RM, Gutierrez O, Houk KN, Synthesis of a trans,syn,trans-dodecahydrophenanthrene via a bicyclic transannular Diels-Alder reaction: intermediate for the synthesis of fusidic acid, J Org Chem, 2010, 75 (20), 6933-40.
Um JM, Kaka NS, Hodgson DM, Houk KN, Transition states and origins of 1,4-asymmetric induction in alkylations of 2,2,6-trialkylpiperidine enamines, Chemistry, 2010, 16 (21), 6310-6.
Steven E. Wheeler, Kendall N. Houk, Paul v. R. Schleyer and Wesley D. Allen, A Hierarchy of Homodesmotic Reactions for Thermochemistry, J. Am. Chem. Soc, 2009, 131 (7), 2547–2560.
Canterbury DP, Herrick IR, Um J, Houk KN, Frontier AJ, A Torquoselective Extrusion of Isoxazoline N-Oxides. Application to the Synthesis of Aryl Vinyl and Divinyl Ketones for Nazarov Cyclization, Tetrahedron. 2009 , 2009, 65 (16), 3165-3179.
Wheeler SE, Moran A, Pieniazek SN, Houk KN, Accurate reaction enthalpies and sources of error in DFT thermochemistry for aldol, Mannich, and alpha-aminoxylation reactions, J Phys Chem A, 2009, 113 (38), 10376-84.
Adam J. T. Smith, Xiyun Zhang, Andrew G. Leach and K. N. Houk, Beyond Picomolar Affinities: Quantitative Aspects of Noncovalent and Covalent Binding of Drugs to Proteins, J. Med. Chem, 2009, 52 (2), 225–233.
Osuna S, Houk KN, Cycloaddition reactions of butadiene and 1,3-dipoles to curved arenes, fullerenes, and nanotubes: theoretical evaluation of the role of distortion energies on activation barriers, Chemistry, 2009, 15 (47), 13219-31.
Osuna S, Houk KN, Cycloaddition reactions of butadiene and 1,3-dipoles to curved arenes, fullerenes, and nanotubes: theoretical evaluation of the role of distortion energies on activation barriers, Chemistry, 2009, 15 (47), 13219-31.
Jackson MI, Han TH, Serbulea L, Dutton A, Ford E, Miranda KM, Houk KN, Wink DA, Fukuto JM, Kinetic feasibility of nitroxyl reduction by physiological reductants and biological implications, Free Radic Biol Med, 2009, 47 (8), 1130-9.
Celebi-Olçüm N, Aviyente V, Houk KN, Mechanism and selectivity of cinchona alkaloid catalyzed [1,3]-shifts of allylic trichloroacetimidates, J Org Chem, 2009, 74 (18), 6944-52.
Krenske EH, Pryor WA, Houk KN, Mechanism of S(H)2 reactions of disulfides: frontside vs backside, stepwise vs concerted, J Org Chem, 2009, 4 (15), 5356-60.
Hakan Gunaydin and K. N. Houk, Mechanisms of Peroxynitrite-Mediated Nitration of Tyrosine, Chem. Res. Toxicol, 2009, 22 (5), 894–898.
Gutierrez O, Iafe RG, Houk KN, Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones, Org Lett, 2009, 11 (19), 4298-301.
Steven E. Wheeler, K. N. Houk , Origin of substituent effects in edge-to-face aryl-aryl interactions , Molecular Physics, 2009, 107 (8-12), 749 - 760 .
Hayden AE, DeChancie J, George AH, Dai M, Yu M, Danishefsky SJ, Houk KN, Origins of the regioselectivities in the Diels-Alder reactions of vinylindenes with 1,4-quinone monoketal and acrolein dienophiles, J Org Chem, 2009, 74 (17), 6770-6.
Smith AJ, Li Y, Houk KN, Quantum mechanics/molecular mechanics investigation of the mechanism of phosphate transfer in human uridine-cytidine kinase 2, Org Biomol Chem, 2009, 7 (13), 2716-24.
Schoenebeck F, Ess DH, Jones GO, Houk KN, Reactivity and regioselectivity in 1,3-dipolar cycloadditions of azides to strained alkynes and alkenes: a computational study, J Am Chem Soc, 2009, 131 (23), 8121-33.
Chen X, Regan CK, Craig SL, Krenske EH, Houk KN, Jorgensen WL, Brauman JI, Steric and solvation effects in ionic S(N)2 reactions, J Am Chem Soc. 2009 Nov 11;131(44):16162-70, 2009, 131 (44), 16162-70.
Wheeler Steven E; Houk K N, Substituent Effects in Cation/pi Interactions and Electrostatic Potentials above the Centers of Substituted Benzenes Are Due Primarily to Through-Space Effects of the Substituents, Journal of the American Chemical Society, 2009, 131 (9), 3126-7.
Yeimy Garcia, Franziska Schoenebeck, Claude Y. Legault, Craig A. Merlic and K. N. Houk, Theoretical Bond Dissociation Energies of Halo-Heterocycles: Trends and Relationships to Regioselectivity in Palladium-Catalyzed Cross-Coupling Reactions, J. Am. Chem. Soc, 2009, 131 (18), 6632–6639.
Franziska Schoenebeck and K. N. Houk, Theoretical Study of the Catalysis of Cyanohydrin Formation by the Cyclic Dipeptide Catalyst cyclo[(S)-His-(S)-Phe], J. Org. Chem, 2009, 74 (4), 1464–1472.
Um JM, Xu H, Houk KN, Tang W, Thermodynamic control of the electrocyclic ring opening of cyclobutenes: C=X substituents at C-3 mask the kinetic torquoselectivity, J Am Chem Soc, 2009, 131 (19), 6664-5.
Alemán C, Betran O, Casanovas J, Houk KN, Hall HK Jr, Thermodynamic control of the polymerizability of five-, six-, and seven-membered lactones, J Org Chem, 2009, 74 (16), 6237-44.
Wheeler SE, Houk KN , Through-Space Effects of Substituents Dominate Molecular Electrostatic Potentials of Substituted Arenes, J Chem Theory Comput, 2009, 5 (9), 2301-2312.
Amy E. Hayden and K. N. Houk, Transition State Distortion Energies Correlate with Activation Energies of 1,4-Dihydrogenations and Diels−Alder Cycloadditions of Aromatic Molecules, J. Am. Chem. Soc., , 2009, 131 (11), 4084–4089.
Gunaydin, H. Houk, K. N., Molecular dynamics prediction of the mechanism of ester hydrolysis in water, J Am Chem Soc, 2008, 130 (46), 15232-3.
Smith, A. J. Muller, R. Toscano, M. D. Kast, P. Hellinga, H. W. Hilvert, D. Houk, K. N., Structural reorganization and preorganization in enzyme active sites: comparisons of experimental and theoretically ideal active site geometries in the multistep serine esterase reaction cycle, J Am Chem Soc, 2008, 130 (46), 15361-73.
Luft, J. A. Winkler, T. Kessabi, F. M. Houk, K. N., Substituent effects on the rearrangements of cyclohexyl to cyclopentyl radicals involving avermectin-related radicals, J Org Chem, 2008, 73 (21), 8175-81.
Celebi-Olcum, N. Ess, D. H. Aviyente, V. Houk, K. N., Effect of Lewis acid catalysts on Diels-Alder and hetero-Diels-Alder cycloadditions sharing a common transition state, J Org Chem, 2008, 73 (19), 7472-80.
Ess, D. H. Hayden, A. E. Klarner, F. G. Houk, K. N., Transition states for the dimerization of 1,3-cyclohexadiene: a DFT, CASPT2, and CBS-QB3 quantum mechanical investigation, J Org Chem, 2008, 73 (19), 7586-92.
Houk, K. N. Cheong, P. H., Computational prediction of small-molecule catalysts, Nature, 2008, 455 (7211), 309-13.
Jones, G. O. Li, X. Hayden, A. E. Houk, K. N. Danishefsky, S. J., The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms, Org Lett, 2008, 10 (18), 4093-6.
Um, J. M. Houk, K. N. Phillips, A. J., Origin of stereoselectivity in the reduction of a planar oxacarbenium, Org Lett, 2008, 10 (17), 3769-72.
Wheeler, S. E. Houk, K. N., Substituent effects in the benzene dimer are due to direct interactions of the substituents with the unsubstituted benzene, J Am Chem Soc, 2008, 130 (33), 10854-5.
Gunaydin, H. Barabash, S. V. Houk, K. N. Ozolins, V., First-principles theory of hydrogen diffusion in aluminum, Phys Rev Lett, 2008, 101 (7), 075901.
Krenske, E. H. Houk, K. N. Arndtsen, B. A. St Cyr, D. J., Cyclic 1,3-dipoles or acyclic phosphonium ylides? Electronic characterization of "Montrealones", J Am Chem Soc, 2008, 130 (31), 10052-3.
Gunaydin, H. Houk, K. N., Molecular dynamics simulation of the HOONO decomposition and the HO*/NO2* caged radical pair in water, J Am Chem Soc, 2008, 130 (31), 10036-7.
Ess, D. H. Houk, K. N., Theory of 1,3-dipolar cycloadditions: distortion/interaction and frontier molecular orbital models, J Am Chem Soc, 2008, 130 (31), 10187-98.
Anderson, C. D. Dudding, T. Gordillo, R. Houk, K. N., Origin of enantioselection in Hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL, Org Lett, 2008, 10 (13), 2749-52.
Ess, D. H. Wheeler, S. E. Iafe, R. G. Xu, L. Celebi-Olcum, N. Houk, K. N., Bifurcations on potential energy surfaces of organic reactions, Angew Chem Int Ed Engl, 2008, 47 (40), 7592-601.
Lin Jiang, Eric A. Althoff, Fernando R. Clemente, Lindsey Doyle, Daniela Rothlisberger, Alexandre Zanghellini, Jasmine L. Gallaher, Jamie L. Betker, Fujie Tanaka, Carlos F. Barbas, III, Donald Hilvert, Kendall N. Houk, Barry L. Stoddard, David Baker, De Novo Computational Design of Retro-Aldol Enzymes, Science, 2008, 319 (5868), 1387-1391.
Pieniazek, S. N. Clemente, F. R. Houk, K. N., Sources of error in DFT computations of C-C bond formation thermochemistries: pi-->sigma transformations and error cancellation by DFT methods, Angew Chem Int Ed Engl, 2008, 47 (40), 7746-9.
Liu, P. Cheong, P. H. Yu, Z. X. Wender, P. A. Houk, K. N., Substituent effects, reactant preorganization, and ligand exchange control the reactivity in Rh(I)-catalyzed (5+2) cycloadditions between vinylcyclopropanes and alkynes, Angew Chem Int Ed Engl, 2008, 47 (21), 3939-41.
Ess, D. H. Jones, G. O. Houk, K. N., Transition states of strain-promoted metal-free click chemistry: 1,3-dipolar cycloadditions of phenyl azide and cyclooctynes, Org Lett, 2008, 10 (8), 1633-6.
Iafe, R. G. Houk, K. N., Intramolecular hetero-Diels-Alder reactions of imine and iminium dienophiles: quantum mechanical exploration of mechanisms and stereoselectivities, J Org Chem, 2008, 73 (7), 2679-86.
Houk, K. N. Jabbari, A. Hall, H. K., Jr. Aleman, C., Why delta-valerolactone polymerizes and gamma-butyrolactone does not, J Org Chem, 2008, 73 (7), 2674-8.
Gunaydin, H. Houk, K. N. Ozolins, V., Vacancy-mediated dehydrogenation of sodium alanate, Proc Natl Acad Sci U S A, 2008, 105 (10), 3673-7.
Wheeler, S. E. Ess, D. H. Houk, K. N., Thinking out of the black box: accurate barrier heights of 1,3-dipolar cycloadditions of ozone with acetylene and ethylene, J Phys Chem A, 2008, 112 (8), 1798-807.
Stanton, C. L. Kuo, I. F. Mundy, C. J. Laino, T. Houk, K. N., QM/MM metadynamics study of the direct decarboxylation mechanism for orotidine-5'-monophosphate decarboxylase using two different QM regions: acceleration too small to explain rate of enzyme catalysis, J Phys Chem B, 2007, 111 (43), 12573-81.
Legault, C. Y. Garcia, Y. Merlic, C. A. Houk, K. N., Origin of regioselectivity in palladium-catalyzed cross-coupling reactions of polyhalogenated heterocycles, J Am Chem Soc, 2007, 129 (42), 12664-5.
Ess, D. H. Houk, K. N., Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity, J Am Chem Soc, 2007, 129 (35), 10646-7.
Natarajan, A. Tsai, C. K. Khan, S. I. McCarren, P. Houk, K. N. Garcia-Garibay, M. A., The photoarrangement of alpha-santonin is a single-crystal-to-single-crystal reaction: a long kept secret in solid-state organic chemistry revealed, J Am Chem Soc, 2007, 129 (32), 9846-7.
Adaligil, E. Davis, B. D. Hilmey, D. G. Shen, Y. Spruell, J. M. Brodbelt, J. S. Houk, K. N. Paquette, L. A., Synthesis of, and structural assignments to the stereoisomers of bis (2,2')- and tris (2,2',2")-tetrahydrofurans: conformational features and ionic binding capacities of these gateway polycyclic networks, J Org Chem, 2007, 72 (16), 6215-23.
Wan, S. Gunaydin, H. Houk, K. N. Floreancig, P. E., An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions, J Am Chem Soc, 2007, 129 (25), 7915-23.
Gunaydin H, Acevedo O, Jorgensen WL, Houk KN , Computation of accurate activation barriers for methyl-transfer reactions of sulfonium and ammonium salts in aqueous solution, Journal of Chemical Theory and Computation, 2007, 3 (3), 1028-1035.
Min SJ, Jones GO, Houk KN, Danishefsky SJ, Creating quaternary centers with high exo stereoselectivity using activated alpha-alkynyl dienophiles , Journal of the American Chemical Society, 2007, 129 (33), 10078-.
Mingji Dai, David Sarlah, Maolin Yu, Samuel J. Danishefsky, Gavin O. Jones, and K. N. Houk, Highly Selective Diels-Alder Reactions of Directly Connected Enyne Dienophiles, J. Am. Chem. Soc, 2007, 129, 645-657.
Dechancie, J. Clemente, F. R. Smith, A. J. Gunaydin, H. Zhao, Y. L. Zhang, X. Houk, K. N., How similar are enzyme active site geometries derived from quantum mechanical theozymes to crystal structures of enzyme-inhibitor complexes? Implications for enzyme design, Protein Sci, 2007, 16 (9), 1851-66.
Michael Winkler and K. N. Houk, Nitrogen-Rich Oligoacenes: Candidates for n-Channel Orgnic Semiconductors, J. Am. Chem. Soc, 2007, 129, 1805-1815.
Wu HP, Ess DH, Lanza S, Weakley TJR, Houk KN, Baldridge KK, Haley MM, Rearrangement of iridabenzvalenes to iridabenzenes and/or eta(5)-cyclopentadienyliridium(I) complexes: Experimental and computational analysis of the influence of silyl ring substituents and phosphine ligands , Organometallics, 2007, 26 (16), 3957-3968.
Koziol L, Winkler M, Houk KN, Venkataramani S, Sander W, Krylov AI , The 1,2,3-tridehydrobenzene triradical: B-2 or not B-2? the answer is (2)A! , Journal of Physical Chemistry A, 2007, 111 (23), 5071-5080.
Chaitanya S. Wannere, Ankan Paul, Rainer Herges, K. N. Houk, Henry F. Schaeffer III, Paul von Rague Schleyer, The Existence of Secondary Orbital Interactions, J. Comp. Chem, 2007, 28, 344-361.
Moss RA, Tian JZ, Sauers RR, Ess DH, Houk KN, Krogh-Jespersen K , The synthesis of dichlorodiazirine and the generation of dichlorocarbene: Spectroscopy and structure of dichlorocarbene ylides, Journal of the American Chemical Society, 2007, 129 (16), 5167-5174.
Jennifer A. R. Luft, Kieche Meleson, and K. N. Houk, Transition Structures of Diastereoselective 1,3-Dipolar Cycloadditions of Nitrile Oxides to Chiral Homoallylic Alcohols, Org. Lett, 2007, 9, 555-558.
Northrop, B. H. Norton, J. E. Houk, K. N., On the mechanism of peripentacene formation from pentacene: computational studies of a prototype for graphene formation from smaller acenes, J Am Chem Soc, 2007, 129 (20), 6536-46.
DeChancie, J. Houk, K. N., The origins of femtomolar protein-ligand binding: hydrogen-bond cooperativity and desolvation energetics in the biotin-(strept)avidin binding site, J Am Chem Soc, 2007, 129 (17), 5419-29.
Celebi-Olcum, N. Ess, D. H. Aviyente, V. Houk, K. N., Lewis acid catalysis alters the shapes and products of bis-pericyclic Diels-Alder transition states, J Am Chem Soc, 2007, 129 (15), 4528-9.
Jarowski, P. D. Houk, K. N. Garcia-Garibay, M. A., Importance of correlated motions on the low barrier rotational potentials of crystalline molecular gyroscopes, J Am Chem Soc, 2007, 129 (11), 3110-7.
Luft, J. A. Meleson, K. Houk, K. N., Transition structures of diastereoselective 1,3-dipolar cycloadditions of nitrile oxides to chiral homoallylic alcohols, Org Lett, 2007, 9 (4), 555-8.
Gordillo, R. Dudding, T. Anderson, C. D. Houk, K. N., Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions, Org Lett, 2007, 9 (3), 501-3.
Jabbari, A. Houk, K. N., Hetero-cope rearrangements of nitrosobutenes. DFT studies of thermal and acid-catalyzed reactions, Org Lett, 2006, 8 (26), 5975-8.
Norton, J. E. Northrop, B. H. Nuckolls, C. Houk, K. N., Why 6-methylpentacene deconjugates but avoids the thermally allowed unimolecular mechanism, Org Lett, 2006, 8 (21), 4915-8.
Chuang, S. C. Clemente, F. R. Khan, S. I. Houk, K. N. Rubin, Y., Approaches to open fullerenes: a 1,2,3,4,5,6-hexaadduct of C60, Org Lett, 2006, 8 (20), 4525-8.
Zhao, Y. L. Suhrada, C. P. Jung, M. E. Houk, K. N., Theoretical investigation of the stereoselective stepwise cope rearrangement of a 3-vinylmethylenecyclobutane, J Am Chem Soc, 2006, 128 (34), 11106-13.
Norton, J. E. Briseno, A. L. Wudl, F. Houk, K. N., Lone-pair orbital interactions in polythiaadamantanes, J Phys Chem A, 2006, 110 (32), 9887-99.
Iafe, R. G. Houk, K. N., Stereoselectivity control by torsional steering in an intramolecular Diels-Alder reaction of vinyl oxocarbenium ions, Org Lett, 2006, 8 (16), 3469-72.
Lee, M. Lloyd, P. Zhang, X. Schallhorn, J. M. Sugimoto, K. Leach, A. G. Sapiro, G. Houk, K. N., Shapes of antibody binding sites: qualitative and quantitative analyses based on a geomorphic classification scheme, J Org Chem, 2006, 71 (14), 5082-92.
Hayden, A. E. Xu, H. Nicolaou, K. C. Houk, K. N., Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone, Org Lett, 2006, 8 (14), 2989-92.
Jabbari, A. Sorensen, E. J. Houk, K. N., Transition states of the retro-ene reactions of allylic diazenes, Org Lett, 2006, 8 (14), 3105-7.
Norton, J. E. Olson, L. P. Houk, K. N., Theoretical studies of quantum amplified isomerizations for imaging systems involving hexamethyl Dewar benzene and related systems, J Am Chem Soc, 2006, 128 (24), 7835-45.
Northrop, B. H. O'Malley, D. P. Zografos, A. L. Baran, P. S. Houk, K. N., Mechanism of the vinylcyclobutane rearrangement of sceptrin to ageliferin and nagelamide E, Angew Chem Int Ed Engl, 2006, 45 (25), 4126-30.
Shih-Ching Chuang, Fernando R. Clemente, Saeed I. Khan, K. N. Houk, and Yves Rubin, Approaches to Open Fullerenes: A 1,2,3,4,5,6-Hexaadduct of C60,, Org. Lett, 2006, 8, 4525-4528.
Bruce N. Hietbrink, Dean J. Tantillo, Kendall N. Houk, and Craig A. Merlic, Chromium Tricarbonyl-Coordinated Carbocations, Carbocation Chemistry, 2006, George A. Olah and G. K. Surya Prakash, eds, 279-289.
Daniel H. Ess, Gavin O. Jones, and K. N. Houk, Conceptual, Qualitative, and Quantitative Theories of 1,3-Dipolar and Diels-Alder Cycloadditions Used in Synthesis, Adv. Synth. Catal, 2006, 348, 2337-2361.
Yoshimitsu Itoh, K. N. Houk, and Koichi Mikami, Experimental and Theoretical Studies on Radical Trifluoromethylation of Titanium Ate and Lithium Enolates, J. Org. Chem, 2006, 71, 8918-8925.
Joseph E. Norton and K. N. Houk, H/Vinyl Conical Intersections of Hexatrienes Related to the Hula-Twist Photoisomerization, Mol. Phys, 2006, 104, 993-1008.
Albert Padwa, Kenneth R. Crawford, Christopher S. Straub, Susan N. Pieniazek, and K. N. Houk, Halo Substituent Effects on Intramolecular Cycloadditions Involving Furanyl Amides, J. Org. Chem, 2006, 71, 5432-5439.
Brian H. Northrop, Daniel P. O'Malley, Alexandros L. Zografos, Phil S. Baran, and K. N. Houk, Mechanism of the Vinylcyclobutane Rearrangement of Sceptrin to Ageliferin and Nagelamide E, Angew. Chem. Int. Ed, 2006, 45, 4126-4130.
Jennifer A. R. Luft, Zhi-Xiang Yu, David L. Hughes, Guy C. Lloyd-Jones, Shane W. Krska, and Kendall N. Houk, On the Stability of the pi-Allyl Intermediate in Molybdenum-Catalyzed Asymmetric Alkylations, Tetrahedron: Asymmetry, 2006, 17, 716-724.
Suzanne E. Paulson, De-Ling Liu, Grazyna E. Orzechowska, Luis M. Campos, and K. N. Houk, Photolysis of Heptanal, J. Org. Chem, 2006, 71, 6403-6408.
Naveen Gandra, Aaron T. Frank, Onica Le Gendre, Nahed Sawwan, David Aebisher, Joel F. Liebman, K. N. Houk, Alexander Greer, and Ruomei Gao, Possible Singlet Oxygen Generation from the Photolysis of Indigo Dyes in Methanol, DMSO, Water, and Ionic Liquid, 1-butyl-3-methylimidazolium Tetrafluoroborate, Tetrahedron, 2006, 62, 10771-10776.
Nicola Edwards, Roger Helgeson, Yi-Lei Zhao, and K. N. Houk, Pyridine-Based Cavitands for Acid and Carboxylate Recognition, Mol. Cryst. Liq. Cryst, 2006, 456, 175-192.
Arash Jabbari, Erik J. Sorensen, and K. N. Houk, Transition States of the Retro-Ene Reactions of Allylic Diazenes, Org. Lett, 2006, 8, 3105-3107.
Jarowski, P. D. Diederich, F. Houk, K. N., Butatrienes as extended alkenes: barriers to internal rotation and substitution effects on the stabilities of the ground states and transition states, J Phys Chem A, 2006, 110 (22), 7237-46.
Branden Brough, Brian H. Northrop, Jacob J. Schmidt, Hsian-Rong Tseng, Kendall N. Houk, J. Fraser Stoddart, and Chih-Ming Ho, "Evaluation of Synthetic Linear Motor-Molecule Actuation Energetics", PNAS, 2006, 103 (23), 8583-8588.
Pryor, W. A. Houk, K. N. Foote, C. S. Fukuto, J. M. Ignarro, L. J. Squadrito, G. L. Davies, K. J. , Free Radical Biology and Medicine: It's a Gas, Man!, Am J Physiol Regul Integr Comp Physiol, 2006.
Cheong, P. H. Yun, H. Danishefsky, S. J. Houk, K. N., Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis, Org Lett, 2006, 8 (8), 1513-6.
Gordillo, R. Houk, K. N., Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones, J Am Chem Soc, 2006, 128 (11), 3543-53.
Dutton, A. S. Suhrada, C. P. Miranda, K. M. Wink, D. A. Fukuto, J. M. Houk, K. N. , Mechanism of pH-dependent decomposition of monoalkylamine diazeniumdiolates to form HNO and NO, deduced from the model compound methylamine diazeniumdiolate, density functional theory, and CBS-QB3 calculations, Inorg Chem, 2006, 45 (6), 2448-56.
Cheong, P. H. Zhang, H. Thayumanavan, R. Tanaka, F. Houk, K. N. Barbas, C. F., 3rd, Pipecolic acid-catalyzed direct asymmetric mannich reactions, Org Lett, 2006, 8 (5), 811-4.
Pieniazek, S. N. Houk, K. N., The origin of the halogen effect on reactivity and reversibility of Diels-Alder cycloadditions involving furan, Angew Chem Int Ed Engl, 2006, 45 (9), 1442-5.
Zhao, Y. L. Houk, K. N., Thionitroxides, RSNHO*: the structure of the SNO moiety in "S-Nitrosohemoglobin", a possible NO reservoir and transporter, J Am Chem Soc, 2006, 128 (5), 1422-3.
Jones, G. O. Guner, V. A. Houk, K. N., Diels-Alder reactions of cyclopentadiene and 9,10-dimethylanthracene with cyanoalkenes: the performance of density functional theory and Hartree-Fock calculations for the prediction of substituent effects, J Phys Chem A Mol Spectrosc Kinet Environ Gen Theory, 2006, 110 (4), 1216-24.
Mitsumori, S. Zhang, H. Ha-Yeon Cheong, P. Houk, K. N. Tanaka, F. Barbas, C. F., 3rd , Direct asymmetric anti-Mannich-type reactions catalyzed by a designed amino acid, J Am Chem Soc, 2006, 128 (4), 1040-1.
Doubleday, C. Suhrada, C. P. Houk, K. N., Dynamics of the degenerate rearrangement of bicyclo[3.1.0]hex-2-ene, J Am Chem Soc, 2006, 128 (1), 90-4.
Northrop, B. H. Houk, K. N., Vinylcyclobutane-cyclohexene rearrangement: theoretical exploration of mechanism and relationship to the Diels-Alder potential surface, J Org Chem, 2006, 71 (1), 3-13.
Miranda, K. M. Katori, T. Torres de Holding, C. L. Thomas, L. Ridnour, L. A. McLendon, W. J. Cologna, S. M. Dutton, A. S. Champion, H. C. Mancardi, D. Tocchetti, C. G. Saavedra, J. E. Keefer, L. K. Houk, K. N. Fukuto, J. M. Kass, D. A. Paolocci, N. Wink, D. A. , Comparison of the NO and HNO donating properties of diazeniumdiolates: primary amine adducts release HNO in Vivo, J Med Chem, 2005, 48 (26), 8220-8.
Zhang, X. Houk, K. N., Acid/base catalysis by pure water: the aldol reaction, J Org Chem, 2005, 70 (24), 9712-6.
Liu, Y. Vignon, S. A. Zhang, X. Bonvallet, P. A. Khan, S. I. Houk, K. N. Stoddart, J. F. , Dynamic chirality in donor-acceptor pretzelanes, J Org Chem, 2005, 70 (23), 9334-44.
Ess, D. H. Houk, K. N., Activation energies of pericyclic reactions: performance of DFT, MP2, and CBS-QB3 methods for the prediction of activation barriers and reaction energetics of 1,3-dipolar cycloadditions, and revised activation enthalpies for a standard set of hydrocarbon pericyclic reactions, J Phys Chem A, 2005, 109 (42), 9542-53.
Dutton, A. S. Fukuto, J. M. Houk, K. N. , Theoretical Reduction Potentials for Nitrogen Oxides from CBS-QB3 Energetics and (C)PCM Solvation Calculations, Inorg Chem, 2005, 44 (21), 7687-8.
Ozturk, C. Aviyente, V. Houk, K. N. , Modeling the stereoselectivity of the Johnson-Claisen rearrangements in the Danishefsky synthesis of gelsemine, J Org Chem, 2005, 70 (18), 7028-34.
Liu, Y. Vignon, S. A. Zhang, X. Houk, K. N. Stoddart, J. F. , Conformational diastereoisomerism in a chiral pretzelane, Chem Commun (Camb), 2005 (31), 3927-9.
Clemente, F. R. Houk, K. N., Theoretical studies of stereoselectivities of intramolecular aldol cyclizations catalyzed by amino acids, J Am Chem Soc, 2005, 127 (32), 11294-302.
Zhao, Y. L. McCarren, P. R. Houk, K. N. Choi, B. Y. Toone, E. J., Nitrosonium-catalyzed decomposition of s-nitrosothiols in solution: a theoretical and experimental study, J Am Chem Soc, 2005, 127 (31), 10917-24.
Palmer, L. C. Zhao, Y. L. Houk, K. N. Rebek, J., Jr. , Diastereoselection of chiral acids in a cylindrical capsule, Chem Commun (Camb), 2005 (29), 3667-9.
Campos, L. M. Warrier, M. V. Peterfy, K. Houk, K. N. Garcia-Garibay, M. A., Secondary alpha isotope effects on deuterium tunneling in triplet o-methylanthrones: extraordinary sensitivity to barrier width, J Am Chem Soc, 2005, 127 (29), 10178-9.
Gavin O. Jones, Daniel H. Ess, and Kendall N. Houk, Activation Energies and Reaction Energetics for 1,3-Dipolar Cycloadditions of Hydrazoic Acid with C-C and C-N Multiple Bonds from High-Accuracy and Density Functional Quantum Mechanical Calculations, Helvetica Chimica Acta, 2005, 7, 1702-1710.
Daniel H. Ess and K. N. Houk, Activation Energies of Pericyclic Reactions: Performance of DFT, MP2, and CBS-QB3 Methods for the Prediction of Activation Barriers and Reaction Energetics of 1,3-Dipolar Cycloadditions, and Revised Activation Enthalpies for a Standard Set of Hydrocarbon Pericyclic Reactions, J. Phys. Chem. A, 2005, 109, 9542-9553.
Yu Takano and K. N. Houk, Benchmarking the Conductor-like Polarizable Continuum Model (CPCM) for Aqueous Solvation Free Energies of Neutral and Ionic Organic Molecules, J. Chem. Theory & Comp, 2005, 1, 70-77.
Yi-Lei Zhao, Walter H. Jones, Frederic Monnat, Fred Wudl, and K. N. Houk, Mechanisms of Thermal Decompositions of Polysulfones: A DFT and CBS-QB3 Study, Macromolecules, 2005, 38, 10279-10285.
Paul Ha-Yeon Cheong and K. N. Houk, Origins and Predictions of Stereoselectivity in Intramolecular Aldol Reactions Catalyzed by Proline Derivatives, Synthesis, 2005, 9, 1533-1537.
Dutton, A. S. Fukuto, J. M. Houk, K. N. , Quantum mechanical determinations of reaction mechanisms, acid base, and redox properties of nitrogen oxides and their donors, Methods Enzymol, 2005, 396, 26-44.
Andrew G. Leach, K. N. Houk, Ian W. Davies, The Origins of Periselectivity and Substituent Effects in Electrocyclizations of o-Nitrostyrenes: A Computational Study, Synthesis, 2005, 19, 3463-3467.
Fukuto, J. M. Dutton, A. S. Houk, K. N. , The chemistry and biology of nitroxyl (HNO): a chemically unique species with novel and important biological activity, Chembiochem, 2005, 6 (4), 612-9.
Fukuto, J. M. Bartberger, M. D. Dutton, A. S. Paolocci, N. Wink, D. A. Houk, K. N. , The physiological chemistry and biological activity of nitroxyl (HNO): the neglected, misunderstood, and enigmatic nitrogen oxide, Chem Res Toxicol, 2005, 18 (5), 790-801.
Ruth Gordillo, Jennifer Carter, and K. N. Houk, Theoretical Explorations of Enantioselectivity Alkylation Reaction of Pyrroles and Indoles Organocatalyzed by Chiral Imidazolidinones, Adv. Synth. & Cat, 2005, 346, 1175-1185.
Zhang, X. Houk, K. N., Why enzymes are proficient catalysts: beyond the Pauling paradigm, Acc Chem Res, 2005, 38 (5), 379-85.
Zhao, Y. L. Bartberger, M. D. Goto, K. Shimada, K. Kawashima, T. Houk, K. N., Theoretical evidence for enhanced NO dimerization in aromatic hosts: implications for the role of the electrophile (NO)(2) in nitric oxide chemistry, J Am Chem Soc, 2005, 127 (22), 7964-5.
Suhrada, C. P. Selcuki, C. Nendel, M. Cannizzaro, C. Houk, K. N. Rissing, P. J. Baumann, D. Hasselmann, D., Dynamic effects on [3,3] and [1,3] shifts of 6-methylenebicyclo[3.2.0]hept-2-ene, Angew Chem Int Ed Engl, 2005, 44 (23), 3548-52.
Dutton, A. S. Fukuto, J. M. Houk, K. N., Theoretical reduction potentials for nitrogen oxides from CBS-QB3 energetics and (C)PCM solvation calculations, Inorg Chem, 2005, 44 (11), 4024-8.
Caramella, P. Quadrelli, P. Toma, L. Romano, S. Khuong, K. S. Northrop, B. Houk, K. N. , The three corrugated surfaces of 1,4-divinyltetramethylene diradical intermediates and their connections to 1,2-divinylcyclobutane, 4-vinylcyclohexene, 1,5-cyclooctadiene, and two butadienes, J Org Chem, 2005, 70 (8), 2994-3008.
Norton, J. E. Houk, K. N., Electronic structures and properties of twisted polyacenes, J Am Chem Soc, 2005, 127 (12), 4162-3.
Khuong, K. S. Beaudry, C. M. Trauner, D. Houk, K. N., Dienophile twisting and substituent effects influence reaction rates of intramolecular Diels-Alder cycloadditions: a DFT study, J Am Chem Soc, 2005, 127 (11), 3688-9.
Jarowski, P. D. Diederich, F. Houk, K. N., Structures and stabilities of diacetylene-expanded polyhedranes by quantum mechanics and molecular mechanics, J Org Chem, 2005, 70 (5), 1671-8.
Khuong, K. S. Jones, W. H. Pryor, W. A. Houk, K. N., The mechanism of the self-initiated thermal polymerization of styrene. Theoretical solution of a classic problem, J Am Chem Soc, 2005, 127 (4), 1265-77.
Zhang, X. Houk, K. N. Leighton, J. L., Origins of stereoselectivity in strain-release allylations, Angew Chem Int Ed Engl, 2005, 44 (6), 938-41.
Miranda, K. M. Dutton, A. S. Ridnour, L. A. Foreman, C. A. Ford, E. Paolocci, N. Katori, T. Tocchetti, C. G. Mancardi, D. Thomas, D. D. Espey, M. G. Houk, K. N. Fukuto, J. M. Wink, D. A. , Mechanism of aerobic decomposition of Angeli's salt (sodium trioxodinitrate) at physiological pH, J Am Chem Soc, 2005, 127 (2), 722-31.
Saphier, S. Hu, Y. Sinha, S. C. Houk, K. N. Keinan, E. , Origin of selectivity in the antibody 20F10-catalyzed Yang cyclization, J Am Chem Soc, 2005, 127 (1), 132-45.
Jung, M. E. Min, S. J. Houk, K. N. Ess, D., Synthesis and relative stability of 3,5-diacyl-4,5-dihydro-1H-pyrazoles prepared by dipolar cycloaddition of enones and alpha-diazoketones, J Org Chem, 2004, 69 (26), 9085-9.
Jarowski, P. D. Wodrich, M. D. Wannere, C. S. Schleyer, P. V. Houk, K. N., How large is the conjugative stabilization of diynes?, J Am Chem Soc, 2004, 126 (46), 15036-7.
Khuong, T. A. Zepeda, G. Sanrame, C. N. Dang, H. Bartberger, M. D. Houk, K. N. Garcia-Garibay, M. A., Crankshaft motion in a highly congested bis(triarylmethyl)peroxide, J Am Chem Soc, 2004, 126 (45), 14778-86.
Guner, V. A. Houk, K. N. Davies, I. W., Computational studies on the electrocyclizations of 1-amino-1,3,5-hexatrienes, J Org Chem, 2004, 69 (23), 8024-8.
Akerling, Z. R. Norton, J. E. Houk, K. N., DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085, Org Lett, 2004, 6 (23), 4273-5.
Clemente, F. R. Houk, K. N., Computational evidence for the enamine mechanism of intramolecular aldol reactions catalyzed by proline, Angew Chem Int Ed Engl, 2004, 43 (43), 5765-8.
Cheong, P. H. Houk, K. N., Origins of selectivities in proline-catalyzed alpha-aminoxylations, J Am Chem Soc, 2004, 126 (43), 13912-3.
Williams, A. R. Northrop, B. H. Houk, K. N. Stoddart, J. F. Williams, D. J., The influence of constitutional isomerism and change on molecular recognition processes, Chemistry, 2004, 10 (21), 5406-21.
Zhao, Y. L. Houk, K. N. Rechavi, D. Scarso, A. Rebek, J., Jr., Equilibrium isotope effects as a probe of nonbonding attractions, J Am Chem Soc, 2004, 126 (37), 11428-9.
Cannizzaro, C. E. Houk, K. N., Theoretical study of the stereoselective additions of chiral alcohols to ketenes, J Am Chem Soc, 2004, 126 (35), 10992-1008.
Black, K. A. Leach, A. G. Kalani, M. Y. Houk, K. N., Antibody-catalyzed oxy-cope rearrangement: mechanism and origins of catalysis and stereoselectivity from DFT quantum mechanics and flexible docking, J Am Chem Soc, 2004, 126 (31), 9695-708.
Yu, Z. X. Wender, P. A. Houk, K. N., On the mechanism of [Rh(CO)2Cl]2-catalyzed intermolecular (5 + 2) reactions between vinylcyclopropanes and alkynes, J Am Chem Soc, 2004, 126 (30), 9154-5.
Vayner, G. Houk, K. N. Jorgensen, W. L. Brauman, J. I., Steric retardation of SN2 reactions in the gas phase and solution, J Am Chem Soc, 2004, 126 (29), 9054-8.
Hu, Y. Houk, K. N. Kikuchi, K. Hotta, K. Hilvert, D., Nonspecific medium effects versus specific group positioning in the antibody and albumin catalysis of the base-promoted ring-opening reactions of benzisoxazoles, J Am Chem Soc, 2004, 126 (26), 8197-205.
Bendikov, M. Duong, H. M. Starkey, K. Houk, K. N. Carter, E. A. Wudl, F., Oligoacenes: theoretical prediction of open-shell singlet diradical ground states, J Am Chem Soc, 2004, 126 (24), 7416-7.
Auffrant, A. Jaun, B. Jarowski, P. D. Houk, K. N. Diederich, F., Peralkynylated buta-1,2,3-trienes: exceptionally low rotational barriers of cumulenic C=C bonds in the range of those of peptide C--N bonds, Chemistry, 2004, 10 (12), 2906-11.
Paul Ha-Yeon Cheong, K. N. Houk, Jayakumar S. Warrier, Stephen Hanessian, Catalysis of the Hajos - Parrish - Eder - Sauer - Wiechert Reaction by cis- and trans-4,5-Methanoprolines: Sensitivity of Proline Catalysis to Pyrrolidine Ring Conformation, Adv. Synth. & Cat, 2004, 346, 1111-1115.
Yu Takano and K. N. Houk, Conformational Preferences in the Transition States and Tetrahedral Intermediates of Transacylations. Relationships to Enzyme-Bound Conformations of Phosphonate Inhibitors of Lipases and Esterases,, J. Phys. Chem. A, 2004, 108, 11740-11751.
Raffaella D'Auria, Richard P. Turco, and K. N. Houk, Effects of Hydration on the Properties of Protonated-Water-Nitric Acid Clusters, J. Phys. Chem, 2004, 108, 3756-3765.
Yilei Zhao, K. N. Houk, and Leif P. Olson, Mechanisms of Peroxynitrous Acid and Methyl Peroxynitrite, ROONO (R = H, Me), Rearrangements: A Conformation-Dependent Homolytic Dissociation, J. Phys. Chem, 2004, 108, 5864-5871.
Vildan A. Guner, Kelli S. Khuong, K. N. Houk, Anthony Chuma, and Peter Pulay, The Performance of the Handy/Cohen Functionals, OLYP and O3LYP, for the Computation of Hydrocarbon Pericyclic Reaction Activation Barriers, J. Phys. Chem. A, 2004, 108, 2959-2965.
Michael Prakesch, Erwan Kerouredan, Danielle Gree, Rene Gree, Jason DeChancie, and K. N. Houk, The Propargylic Route as Efficient Entry to Monofluoro and Gem-Difluoro Compounds: Mechanistic Considerations, J. Fluorine Chem, 2004, 15 (4), 537-541.
Allemann, C. Gordillo, R. Clemente, F. R. Cheong, P. H. Houk, K. N., Theory of asymmetric organocatalysis of Aldol and related reactions: rationalizations and predictions, Acc Chem Res, 2004, 37 (8), 558-69.
V. Maggiotti, S. Bahmanyar, M. Reiter, M. Resmini, K. N. Houk, and V. Gouverneur, Unusual Reversal of Regioselectivity in Antibody-Mediated Aldol Additions with Unsymmetrical Methyl Ketones, Tetrahedron, 2004, 60, 619-632.
K. N. Houk, Dean J. Tantillo, Courtney Stanton, and Yunfeng Hu, What Have Theory and Crystallography Revealed About the Mechanism of Catalysis by Orotidine Monophosphate Decarboxylase?, Top. Curr. Chem, 2004, 238, 1-22.
Leach, A. G. Houk, K. N. Reymond, J. L. , Theoretical investigation of the origins of catalysis of a retro-Diels-Alder reaction by antibody 10F11, J Org Chem, 2004, 69 (11), 3683-92.
Dudding, T. Houk, K. N., Computational predictions of stereochemistry in asymmetric thiazolium- and triazolium-catalyzed benzoin condensations, Proc Natl Acad Sci U S A, 2004, 101 (16), 5770-5.
Tantillo, D. J. Hoffmann, R. Houk, K. N. Warner, P. M. Brown, E. C. Henze, D. K. , Extended barbaralanes: sigmatropic shiftamers or sigma-polyacenes?, J Am Chem Soc, 2004, 126 (13), 4256-63.
Dutton, A. S. Fukuto, J. M. Houk, K. N., Mechanisms of HNO and NO production from Angeli's salt: density functional and CBS-QB3 theory predictions, J Am Chem Soc, 2004, 126 (12), 3795-800.
Davies, I. W. Guner, V. A. Houk, K. N. , Theoretical evidence for oxygenated intermediates in the reductive cyclization of nitrobenzenes, Org Lett, 2004, 6 (5), 743-6.
Davies, I. W. Marcoux, J. F. Kuethe, J. T. Lankshear, M. D. Taylor, J. D. Tsou, N. Dormer, P. G. Hughes, D. L. Houk, K. N. Guner, V. , Demonstrating the synergy of synthetic, mechanistic, and computational studies in a regioselective aniline synthesis, J Org Chem, 2004, 69 (4), 1298-308.
Dutton, A. S. Fukuto, J. M. Houk, K. N., The mechanism of NO formation from the decomposition of dialkylamino diazeniumdiolates: density functional theory and CBS-QB3 predictions, Inorg Chem, 2004, 43 (3), 1039-45.
Vayner, G. Houk, K. N. Sun, Y. K., Origins of enantioselectivity in reductions of ketones on cinchona alkaloid modified platinum, J Am Chem Soc, 2004, 126 (1), 199-203.
Limanto, J. Khuong, K. S. Houk, K. N. Snapper, M. L. , Intramolecular cycloadditions of cyclobutadiene with dienes: experimental and computational studies of the competing (2 + 2) and (4 + 2) modes of reaction, J Am Chem Soc, 2003, 125 (52), 16310-21.
Yu, Z. X. Caramella, P. Houk, K. N., Dimerizations of nitrile oxides to furoxans are stepwise via dinitrosoalkene diradicals: a density functional theory study, J Am Chem Soc, 2003, 125 (50), 15420-5.
Hamilton, D. S. Zhang, X. Ding, Z. Hubatsch, I. Mannervik, B. Houk, K. N. Ganem, B. Creighton, D. J. , Mechanism of the glutathione transferase-catalyzed conversion of antitumor 2-crotonyloxymethyl-2-cycloalkenones to GSH adducts, J Am Chem Soc, 2003, 125 (49), 15049-58.
Khuong, K. S. Houk, K. N., One-bond, two-bond, and three-bond mechanisms in thermal deazetizations of 2,3-diazabicyclo[2.2.2]oct-2-enes, trans-azomethane, and 2,3-diazabicyclo[2.2.1]hept-2-ene, J Am Chem Soc, 2003, 125 (48), 14867-83.
Prakesch, M. Gree, D. Gree, R. Carter, J. Washington, I. Houk, K. N. , Stereoselectivity of nitrile oxide cycloadditions to chiral allylic fluorides: experiment and theory, Chemistry, 2003, 9 (22), 5664-72.
Yu, Z. X. Houk, K. N., Intramolecular 1,3-dipolar ene reactions of nitrile oxides occur by stepwise 1,1-cycloaddition/retro-ene mechanisms, J Am Chem Soc, 2003, 125 (45), 13825-30.
Houk, K. N. Leach, A. G. Kim, S. P. Zhang, X., Binding affinities of host-guest, protein-ligand, and protein-transition-state complexes, Angew Chem Int Ed Engl, 2003, 42 (40), 4872-97.
Jung, M. E. van den Heuvel, A. Leach, A. G. Houk, K. N., Unexpected syn hydride migration in the non-aldol aldol reaction, Org Lett, 2003, 5 (19), 3375-8.
Cho, J. Y. Dutton, A. Miller, T. Houk, K. N. Fukuto, J. M., Oxidation of N-hydroxyguanidines by copper(II): model systems for elucidating the physiological chemistry of the nitric oxide biosynthetic intermediate N-hydroxyl-L-arginine, Arch Biochem Biophys, 2003, 417 (1), 65-76.
Washington, I. Houk, K. N. Armstrong, A., Strategies for the design of organic aziridination reagents and catalysts: transition structures for alkene aziridinations by NH transfer, J Org Chem, 2003, 68 (17), 6497-501.
Tuzun, N. S. Aviyente, V. Houk, K. N. , A theoretical study on the mechanism of the cyclopolymerization of diallyl monomers, J Org Chem, 2003, 68 (16), 6369-74.
Leach, A. G. Goldstein, E. Houk, K. N., A cornucopia of cycloadducts: theoretical predictions of the mechanisms and products of the reactions of cyclopentadiene with cycloheptatriene, J Am Chem Soc, 2003, 125 (27), 8330-9.
Vogel, E. Michels, M. Zander, L. Lex, J. Tuzun, N. S. Houk, K. N. , Spirodiporphyrins--as binuclear metal complexes, Angew Chem Int Ed Engl, 2003, 42 (25), 2857-62.
Vildan Guner, Kelli S. Khuong, Andrew G. Leach, Patrick S. Lee, Michael D. Bartberger, and K. N. Houk, A Standard Set of Pericyclic Reactions of Hydrocarbons for the Benchmarking of Computational Methods: The Performance of ab Initio, Density Functional, CASSCF, CASPT2, and CBS-QB3 Methods for the Prediction of Activation Barriers, Reaction Energetics, and Transition State Geometries, J. Phys. Chem A, 2003, 107, 11445-11459.
Hiroshi Isobe, Yu Takano, Yasutaka Kitagawa, Takashi Kawakami, Syusuke Yamanaka, Kizashi Yamaguchi, and K. N. Houk, Systematic Comparisons between Broken-Symmetry and Symmetry-Adapted Approaches to Transition States by Chemical Indices: A Case Study of the Diels-Alder Reactions, J. Phys. Chem. A, 2003, 107, 682-694.
Houk, K. N. Hietbrink, B. N. Bartberger, M. D. McCarren, P. R. Choi, B. Y. Voyksner, R. D. Stamler, J. S. Toone, E. J., Nitroxyl disulfides, novel intermediates in transnitrosation reactions, J Am Chem Soc, 2003, 125 (23), 6972-6.
Black, K. A. Wilsey, S. Houk, K. N. , Dissociative and associative mechanisms of cope rearrangements of fluorinated 1,5-hexadienes and 2,2'-bis-methylenecyclopentanes, J Am Chem Soc, 2003, 125 (22), 6715-24.
Zhu, X. Heine, A. Monnat, F. Houk, K. N. Janda, K. D. Wilson, I. A. , Structural basis for antibody catalysis of a cationic cyclization reaction, J Mol Biol, 2003, 329 (1), 69-83.
Lee, P. S. Sakai, S. Horstermann, P. Roth, W. R. Kallel, E. A. Houk, K. N., Altering the allowed/forbidden gap in cyclobutene electrocyclic reactions: experimental and theoretical evaluations of the effect of planarity constraints, J Am Chem Soc, 2003, 125 (19), 5839-48.
Zhang, X. Houk, K. N. Lin, S. Danishefsky, S. J. , Mechanism of cis-enamide formation from N-(alpha-silyl)allyl amides: synthetic potential of stepwise dyotropic rearrangements, J Am Chem Soc, 2003, 125 (17), 5111-4.
Lee, P. S. Zhang, X. Houk, K. N., Origins of inward torquoselectivity by silyl groups and other sigma-acceptors in electrocyclic reactions of cyclobutenes, J Am Chem Soc, 2003, 125 (17), 5072-9.
Leach, A. G. Houk, K. N., The mechanism and regioselectivity of the ene reactions of nitroso compounds: a theoretical study of reactivity, regioselectivity, and kinetic isotope effects establishes a stepwise path involving polarized diradical intermediates, Org Biomol Chem, 2003, 1 (8), 1389-403.
Bahmanyar, S. Houk, K. N., Origins of opposite absolute stereoselectivities in proline-catalyzed direct Mannich and aldol reactions, Org Lett, 2003, 5 (8), 1249-51.
Leach, A. G. Wang, R. Wohlhieter, G. E. Khan, S. I. Jung, M. E. Houk, K. N., Theoretical elucidation of kinetic and thermodynamic control of radical addition regioselectivity, J Am Chem Soc, 2003, 125 (14), 4271-8.
Olson, L. P. Bartberger, M. D. Houk, K. N. , Peroxynitrate and peroxynitrite: a complete basis set investigation of similarities and differences between these NOx species, J Am Chem Soc, 2003, 125 (13), 3999-4006.
Haeffner, F. Houk, K. N. Schulze, S. M. Lee, J. K. , Concerted rearrangement versus heterolytic cleavage in anionic [2,3]- and [3,3]-sigmatropic shifts. A DFT study of relationships among anion stabilities, mechanisms, and rates, J Org Chem, 2003, 68 (6), 2310-6.
Cannizzaro, C. E. Ashley, J. A. Janda, K. D. Houk, K. N. , Experimental determination of the absolute enantioselectivity of an antibody-catalyzed Diels-Alder reaction and theoretical explorations of the origins of stereoselectivity, J Am Chem Soc, 2003, 125 (9), 2489-506.
Bahmanyar, S. Houk, K. N. Martin, H. J. List, B. , Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions, J Am Chem Soc, 2003, 125 (9), 2475-9.
Yu, Z. X. Houk, K. N., Why trimerization? Computational elucidation of the origin of selective trimerization of ethene catalyzed by [TaCl3(CH3)2] and an agostic-assisted hydride transfer mechanism, Angew Chem Int Ed Engl, 2003, 42 (7), 808-11.
Singleton, D. A. Hang, C. Szymanski, M. J. Meyer, M. P. Leach, A. G. Kuwata, K. T. Chen, J. S. Greer, A. Foote, C. S. Houk, K. N. , Mechanism of ene reactions of singlet oxygen. A two-step no-intermediate mechanism, J Am Chem Soc, 2003, 125 (5), 1319-28.
Khaledy, M. M. Kalani, M. Y. Khuong, K. S. Houk, K. N. Aviyente, V. Neier, R. Soldermann, N. Velker, J. , Origins of boat or chair preferences in the Ireland-Claisen rearrangements of cyclohexenyl esters: a theoretical study, J Org Chem, 2003, 68 (2), 572-7.
Ujaque, G. Tantillo, D. J. Hu, Y. Houk, K. N. Hotta, K. Hilvert, D. , Catalysis on the coastline: theozyme, molecular dynamics, and free energy perturbation analysis of antibody 21D8 catalysis of the decarboxylation of 5-nitro-3-carboxybenzisoxazole, J Comput Chem, 2003, 24 (1), 98-110.
Hoang, L. Bahmanyar, S. Houk, K. N. List, B. , Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions, J Am Chem Soc, 2003, 125 (1), 16-7.
Leach, A. G. Houk, K. N., The ene reactions of nitroso compounds involve polarized diradical intermediates, J Am Chem Soc, 2002, 124 (50), 14820-1.
Zhang, X. Deng, Q. Yoo, S. H. Houk, K. N., Origins and predictions of stereoselective antibody catalysis: theoretical analysis of Diels-Alder catalysis by 39A11 and its germ-line antibody, J Org Chem, 2002, 67 (25), 9043-53.
Limanto, J. Tallarico, J. A. Porter, J. R. Khuong, K. S. Houk, K. N. Snapper, M. L. , Intramolecular cycloadditions of cyclobutadiene with olefins, J Am Chem Soc, 2002, 124 (49), 14748-58.
Ujaque, G. Norton, J. E. Houk, K. N., Electrostatic interactions between substituents as regioselectivity control elements in Diels-Alder cycloadditions. A DFT study of cycloadditions of 1-methoxy-4-trimethylsiloxy dienes with acrylonitrile, J Org Chem, 2002, 67 (21), 7179-84.
Wilsey, S. Houk, K. N. , "H/Vinyl" and "Alkyl/Vinyl" conical intersections leading to carbene formation from the excited states of cyclohexene and norbornene, J Am Chem Soc, 2002, 124 (37), 11182-90.
Schindele, C. Houk, K. N. Mayr, H. , Relationships between carbocation stabilities and electrophilic reactivity parameters, E: quantum mechanical studies of benzhydryl cation structures and stabilities, J Am Chem Soc, 2002, 124 (37), 11208-14.
Bartberger, M. D. Liu, W. Ford, E. Miranda, K. M. Switzer, C. Fukuto, J. M. Farmer, P. J. Wink, D. A. Houk, K. N., The reduction potential of nitric oxide (NO) and its importance to NO biochemistry, Proc Natl Acad Sci U S A, 2002, 99 (17), 10958-63.
Olson, L. P. Kuwata, K. T. Bartberger, M. D. Houk, K. N. , Conformation-dependent state selectivity in O-O cleavage of ONOONO: an "inorganic cope rearrangement" helps explain the observed negative activation energy in the oxidation of nitric oxide by dioxygen, J Am Chem Soc, 2002, 124 (32), 9469-75.
Washington, I. Houk, K. N., Epoxidations by peracid anions in water: ambiphilic oxenoid reactivity and stereoselectivity, Org Lett, 2002, 4 (16), 2661-4.
Ujaque, G. Lee, P. S. Houk, K. N. Hentemann, M. F. Danishefsky, S. J., The origin of endo stereoselectivity in the hetero-Diels-Alder reactions of aldehydes with ortho-xylylenes: CH-pi, pi-pi, and steric effects on stereoselectivity, Chemistry, 2002, 8 (15), 3423-30.
Suhrada, C. P. Houk, K. N., Potential surface for the quadruply degenerate rearrangement of bicyclo[3.1.0]hex-2-ene, J Am Chem Soc, 2002, 124 (30), 8796-7.
Tuzun, N. S. Aviyente, V. Houk, K. N. , Theoretical study of factors controlling rates of cyclization of radical intermediates from diallylamine and diallylammonium monomers in radical polymerizations, J Org Chem, 2002, 67 (15), 5068-75.
Leach, A. G. Houk, K. N., Diels-Alder and ene reactions of singlet oxygen, nitroso compounds and triazolinediones: transition states and mechanisms from contemporary theory, Chem Commun (Camb), 2002, volume (12), 1243-55.
Cannizzaro, C. E. Houk, K. N., Magnitudes and chemical consequences of R(3)N(+)-C-H...O[double bond]C hydrogen bonding, J Am Chem Soc, 2002, 124 (24), 7163-9.
H. Isobe, Y. Takano, Y. Kitagawa, T. Kawakami, S. Yamanaka, K. Yamaguchi, and K. N. Houk, Extended Hartree-Fock (EHF) Theory of Chemical Reactions VI: Hybrid DFT and Post-Hartree-Fock Approaches for Concerted and Non-Concerted Transition Structures of the Diels-Alder Reaction, Mol. Phys, 2002, 100, 717-727.
Wilsey, S. Houk, K. N. , H-vinyl conical intersections for dienes: a mechanism for the photochemical hula twists, Photochem Photobiol, 2002, 76 (6), 616-21.
Kim, S. P. Leach, A. G. Houk, K. N., The origins of noncovalent catalysis of intermolecular Diels-Alder reactions by cyclodextrins, self-assembling capsules, antibodies, and RNAses, J Org Chem, 2002, 67 (12), 4250-60.
Leach, A. G. Catak, S. Houk, K. N., Mechanism of the forbidden [3s,5s]-sigmatropic shift: orbital symmetry influences stepwise mechanisms involving diradical intermediates, Chemistry, 2002, 8 (6), 1290-9.
Tantillo, D. J. Houk, K. N., Transition state docking: a probe for noncovalent catalysis in biological systems. Application to antibody-catalyzed ester hydrolysis, J Comput Chem, 2002, 23 (1), 84-95.
Bahmanyar, S. Houk, K. N., The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions, J Am Chem Soc, 2001, 123 (51), 12911-2.
Washington, I. Houk, K. N., CH.O Hydrogen Bonding Influences pi-Facial Stereoselective Epoxidations We are grateful to the National Institute of General Medical Sciences, National Institutes of Health (GM-36700) for financial support of this research and the National Computational Science Alliance (Illinois) for computer time and support, Angew Chem Int Ed Engl, 2001, 40 (23), 4485-4488.
Bahmanyar, S. Houk, K. N., Transition states of amine-catalyzed aldol reactions involving enamine intermediates: theoretical studies of mechanism, reactivity, and stereoselectivity, J Am Chem Soc, 2001, 123 (45), 11273-83.
Merlic, C. A. Hietbrink, B. N. Houk, K. N., Donor and acceptor properties of the chromium tricarbonyl substituent in benzylic and homobenzylic anions, cations, and radicals, J Org Chem, 2001, 66 (20), 6738-44.
Walker, M. J. Hietbrink, B. N. Thomas, B. E. th Nakamura, K. Kallel, E. A. Houk, K. N., Torquoselectivity induced by lone-pair conjugation in the electrocyclic reactions of 1-azapolyenes, J Org Chem, 2001, 66 (20), 6669-72.
Bartberger, M. D. Mannion, J. D. Powell, S. C. Stamler, J. S. Houk, K. N. Toone, E. J., S-N dissociation energies of S-nitrosothiols: on the origins of nitrosothiol decomposition rates, J Am Chem Soc, 2001, 123 (36), 8868-9.
Houk, K. N. Lee, P. S. Nendel, M., Polyacene and cyclacene geometries and electronic structures: bond equalization, vanishing band gaps, and triplet ground states contrast with polyacetylene, J Org Chem, 2001, 66 (16), 5517-21.
Leach, A. G. Houk, K. N., Transition states and mechanisms of the hetero-Diels-Alder reactions of hyponitrous acid, nitrosoalkanes, nitrosoarenes, and nitrosocarbonyl compounds, J Org Chem, 2001, 66 (15), 5192-200.
Tantillo, D. J. Houk, K. N., Canonical binding arrays as molecular recognition elements in the immune system: tetrahedral anions and the ester hydrolysis transition state, Chem Biol, 2001, 8 (6), 535-45.
Green, N. S. Reisler, E. Houk, K. N., Quantitative evaluation of the lengths of homobifunctional protein cross-linking reagents used as molecular rulers, Protein Sci, 2001, 10 (7), 1293-304.
Merlic, C. A. Miller, M. M. Hietbrink, B. N. Houk, K. N., Reactivity of (eta(6)-arene)tricarbonylchromium complexes toward additions of anions, cations, and radicals, J Am Chem Soc, 2001, 123 (21), 4904-18.
Chen, J. Wang, R. Taussig, M. Houk, K. N., Quantitative calculations of antibody--antigen binding: steroid--DB3 binding energies by the linear interaction energy method, J Org Chem, 2001, 66 (9), 3021-6.
Radkiewicz, J. L. Zipse, H. Clarke, S. Houk, K. N., Neighboring side chain effects on asparaginyl and aspartyl degradation: an ab initio study of the relationship between peptide conformation and backbone NH acidity, J Am Chem Soc, 2001, 123 (15), 3499-506.
Rubin, Y. Jarrosson, T. Wang, G. W. Bartberger, M. D. Houk, K. N. Schick, G. Saunders, M. Cross, R. J., Cover Picture, Angew Chem Int Ed Engl, 2001, 40 (8), 1321.
Rubin, Y. Jarrosson, T. Wang, G. W. Bartberger, M. D. Houk, K. N. Schick, G. Saunders, M. Cross, R. J., Insertion of Helium and Molecular Hydrogen Through the Orifice of an Open Fullerene This work was supported by grants from the National Science Foundation, Angew Chem Int Ed Engl, 2001, 40 (8), 1543-1546.
Gree, D. Vallerie, L. Gree, R. Toupet, L. Washington, I. Pelicier, J. P. Villacampa, M. Perez, J. M. Houk, K. N., Conformations of allylic fluorides and stereoselectivities of their diels-alder cycloadditions, J Org Chem, 2001, 66 (7), 2374-81.
Tantillo, D. J. Houk, K. N. Jung, M. E., Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers, J Org Chem, 2001, 66 (6), 1938-40.
Bartberger, M. D. Fukuto, J. M. Houk, K. N., On the acidity and reactivity of HNO in aqueous solution and biological systems, Proc Natl Acad Sci U S A, 2001, 98 (5), 2194-8.
Houk, K. N. Lee, J. K. Tantillo, D. J. Bahmanyar, S. Hietbrink, B. N., Crystal structures of orotidine monophosphate decarboxylase: does the structure reveal the mechanism of nature's most proficient enzyme?, Chembiochem, 2001, 2 (2), 113-8.
Behnam, S. M. Behnam, S. E. Ando, K. Green, N. S. Houk, K. N., Stereoelectronic, torsional, and steric effects on rates of enolization of ketones, J Org Chem, 2000, 65 (26), 8970-8.
Nendel, M. Sperling, D. Wiest, O. Houk, K. N., Computational explorations of vinylcyclopropane-cyclopentene rearrangements and competing diradical stereoisomerizations, J Org Chem, 2000, 65 (11), 3259-68.