Publications

Edward R. Thornton

(83) Neelamkavil, S.; Arison, B.; Birzin, E.; Feng, J.-J.; Chen, K.-H.; Lin, A.; Cheng, F.-C.; Taylor, L.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. J. Med. Chem. 2005, 48, 4025-4030. "Replacement of Phe6, Phe7, and Phe11 of D-Trp8-Somatostatin-14 with L-Pyrazinylalanine. Predicted and Observed Effects on Binding Affinities at hSST2 and hSST4. An Unexpected Effect of the Chirality of Trp8 on NMR Spectra in Methanol."

(82) Angeles, A. R.; Neagu, I.; Birzin, E. T.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. Org. Lett. 2005, 7, 1121-1124. "Synthesis and Binding Affinities of Novel SRIF-Mimicking beta-D-Glucosides Satisfying the Requirement for a pi-Cloud at C1."

(81) Neelamkavil, S.; Mowery, B.P.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. J. Pept. Res. 2005, 65, 139-142. "A Practical Synthesis of Nalpha-Fmoc-L-pyrazinylalanine via Schöllkopf’s Chiral Auxiliary."

(80) Turowski, M.; Yamakawa, N.; Meller, J.; Kimata, K.; Ikegami, T.; Hosoya, K.; Tanaka, N.; Thornton, E. R. J. Am. Chem. Soc. 2003, 125, 13836-13849. "Deuterium Isotope Effects on Hydrophobic Interactions: The Importance of Dispersion Interactions in the Hydrophobic Phase."

(79) Prasad, V.; Birzin, E. T.; McVaugh, C. T.; van Rijn, R. D.; Rohrer, S. P.; Chicchi, G.; Underwood, D. J.; Thornton, E. R.; Smith, A. B., III; Hirschmann, R. J. Med. Chem. 2003, 46, 1858-1869. "Effects of Heterocyclic Aromatic Substituents on Binding Affinities at Two Distinct Sites of Somatostatin Receptors. Correlation with the Electrostatic Potential of Substituents."

(78) Przeslawski, R. M.; Newman, S.; Thornton, E. R.; Joullie, M. M. Syn. Commun. 1995, 25, 2975-2980. "A short, Affordable, One-Pot synthesis of a Camphor-Derived Amino Alcohol."

(77) Choudhury, A.; Thornton, E. R. Tetrahedron Lett. 1993, 34, 2221-2224, "alpha´-Benzoyloxy and alpha´-Methoxymethoxy Lithium Enolates Giving Opposite Diastereofacial Selectivities in Aldol Reactions. Use of (Probable) Extended Chelation for Reversal of Stereoselectivities."

(76) Das, G.; Thornton, E. R. J. Am. Chem. Soc. 1993, 115, 1302-1312, "Aldol Additions of Pinacolone Lithium Enolate with Ketones: Reactivities Governed Predominantly by Field Effects."

(75) Choudhury, A.; Thornton, E. R. Tetrahedron 1992, 48, 5701-5708, "Asymmetric Aldol Reactions of an alpha´-Benzoyl Titanium Enolate." [invited paper]

(74) Reddy, D. R.; Thornton, E. R., J. Chem. Soc., Chem. Commun. 1992, 172-173, "A Very Mild, Catalytic and Versatile Procedure for alpha-Oxidation of Ketone Silyl Enol Ethers Using (salen)Manganese(III) Complexes; A New, Chiral Complex Giving Asymmetric Induction. A Possible Model for Selective Biochemical Oxidative Reactions Through Enol Formation."

(73) Siegel, C.; Thornton, E. R., Tetrahedron: Asymmetry 1991, 2, 1413-1428, "Diels-Alder Reactions with Dienes Bearing a Remote Stereogenic Center. Conformational Model for Diastereofacial Selectivity." [invited paper]

(72) Das, G.; Thornton, E. R., Tetrahedron Lett. 1991, 32, 5239-5242, "Large Rate Accelerations in Aldol Reaction of ortho-Substituted Benzaldehydes."

(71) Tripathy, R.; Carroll, P. J.; Thornton, E. R., J. Am. Chem. Soc. 1991, 113, 7630-7640, "Diene-Dienophile Hydrogen-Bonding Control of Diels-Alder Reactions with Dienes Bearing a Remote Stereogenic Center. Amplification of the Receptor Nature of Dienes by Conformational Tuning Leading to High Diastereofacial Discrimination."

(70) Prapansiri, V.; Thornton, E. R., Tetrahedron Lett. 1991, 32, 3147-3150, "Asymmetric Diels -Alder Reactions. Inverse Electron Demand Reactions of Esters of 3-Hydroxypyran-2-one with Vinyl Ethers: Use of High Pressure to Avoid Decarboxylation of Adducts."

(69) Nerz-Stormes, M.; Thornton, E. R., J. Org. Chem. 1991, 56, 2489-2498, "Asymmetric Aldol Reactions. Use of the Titanium Enolate of a Chiral N-Acyloxazolidinone to Reverse Diastereofacial Selectivities."

(68) Bonner, M. P.; Thornton, E. R., J. Am. Chem. Soc. 1991, 113, 1299-1308, "Asymmetric Aldol Reactions. A New Camphor-Derived Chiral Auxiliary Giving Highly Stereoselective Aldol Reactions of Both Lithium and Titanium(IV) Enolates."

(67) Panyachotipun, C.; Thornton, E. R., Tetrahedron Lett. 1990, 31, 6001-6004, "Steric Influence of Silyl Groups in Titanium- and Lithium-Mediated Aldol Condensations."

(66) Tripathy, R.; Carroll, P. J.; Thornton, E. R., J. Am. Chem. Soc. 1990, 112, 6743-6744, "Asymmetric Diels-Alder Reactions with Chiral Dienes. Control of Facial Selectivity Through Hydrogen Bonding."

(65) Shirodkar, S.; Nerz-Stormes, M.; Thornton, E. R., Tetrahedron Lett. 1990, 31, 4699-4702, "Asymmetric Aldol Reactions. Mechanism of Solvent Effect on Stereoselectivity Is Specific, Stoichiometric Binding of Tetrahydrofuran to a Chiral Titanium Enolate."

(64) Das, G.; Thornton, E. R. J. Am. Chem. Soc. 1990, 112, 5360-5362, "Extremely High Rate Accelerations in Aldol Reactions of alpha-Alkoxyketones: Reactivity Governed by Substituent Field Effects."

(63) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722-5728, "Asymmetric Aldol Reactions. A Titanium Enolate Giving Very High Diastereofacial Selectivities."

(62) Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1988, 29, 5225-5228, "Conformational Model for Asymmetric Diels-Alder Reactions with Chiral Dienes."

(61) March, P. E.; Antonian, E.; Schneider, D. M.; Rothwarf, D. M.; Thornton, E. R. Neurochem. Res. 1987, 12, 635-640, "The High Molecular Weight Proteins of Bovine Brain Plain Synaptic Vesicles."

(60) Nerz-Stormes, M.; Thornton, E. R. Tetrahedron Lett. 1986, 27, 897-900, "Apparent Chelation Control in Aldol Reactions of Chiral (Me2CHO)3Ti-Enolates."

(59) Siegel, C.; Thornton E. R. Tetrahedron Lett. 1986, 27, 457-460, "Very High Diastereofacial Selectivities in Convenient Titanium-Mediated Aldol Reactions."

(58) Antonian, E.; Thornton, E. R. Eur. J. Biochem. 1984, 145, 511-517, "Extensive Cross-Linking of Calf Brain Plain Synaptic Vesicle Proteins."

(57) Nerz-Stormes, M.; Thornton, E. R. J. Am. Chem. Soc. 1984, 106, 5240-5246, "Carbon-13 Spin-Lattice Relaxation Studies of GD1a Micelles. Limited Segmental Motion of Head Group Saccharide Units."

(56) Wydila, J.; Thornton, E. R. J. Org. Chem. 1984, 49, 244-249, "Synthesis and Photochemical Studies of a Diazomalonyl-Containing Galactocerebroside Analogue. A Glycolipid Photolabeling Reagent."

(55) Keilbaugh, S. A.; Thornton, E. R. Biochemistry 1983, 22, 5063-5068, "Photolysis of Cholesteryl Diazoacetate in Small Unilamellar Vesicles."

(54) Keilbaugh, S. A.; Thornton, E. R. J. Am. Chem. Soc. 1983, 105, 3283-3286, "Synthesis and Photoreactivity of Cholesteryl Diazoacetate: A Novel Photolabeling Reagent."

(53) March, P. E.; Thornton, E. R. Biochem. Biophys. Res. Commun. 1983, 110, 804-810, "Binding of Concanavalin A to Calf Brain Synaptic Vesicles."

(52) Wydila, J.; Thornton, E. R. Tetrahedron Lett. 1983, 24, 233-236, "Photolysis Studies of alpha-Diazoamides. The Effect of Carboxamide Substituents on Selectivity Ratios."

(51) Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393-4398, "Useful Syntheses of erythro- and threo-N-Oleoyl-D-sphingosines (Ceramides) and Galactosylceramides (Cerebrosides) from L-Serine."

(50) Tkaczuk, P.; Thornton, E. R. Biochem. Biophys. Res. Commun. 1979, 91, 1415-1422, "Carbon-13 Nuclear Magnetic Resonance Studies of Cerebroside Derivatives and Their Properties in Lecithin Bilayers."

(49) Harris, P. L.; Thornton, E. R. J. Am. Chem. Soc. 1978, 100, 6738-6745, "Carbon-13 and Proton Nuclear Magnetic Resonance Studies of Gangliosides."

(48) Thornton, E. K.; Thornton, E. R. In Transition States of Biochemical Processes; Gandour, R. D.; Schowen, R. L., Eds.; Plenum Press: New York, 1978, Chapter 1, pp. 3-76, "Scope and Limitations of the Concept of the Transition State."

(47) Su, D. T. T.; Thornton, E. R. J. Am. Chem. Soc. 1978, 100, 1872-1875, "Pull-Push Mechanism for the 1,2-Hydrogen Rearrangement of Carbenes. Substituent and Deuterium Isotope Effects for Thermal Decomposition of 1-Phenyl-2-diazopropanes."

(46) Czarniecki, M. F.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8279-8282, "Carbon-13 Nuclear Magnetic Resonance of Ganglioside Sugars. Spin-Lattice Relaxation Probes for Structure and Microdynamics of Cell Surface Carbohydrates."

(45) Czarniecki, M. F.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8273-8279, "Carbon-13 Nuclear Magnetic Resonance Spin-Lattice Relaxation in the N-Acylneuraminic Acids. Probes for Internal Dynamics and Conformational Analysis."

(44) Tanaka, N.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 7300-7307, "Structural and Isotopic Effects in Hydrophobic Binding Measured by High-Pressure Liquid Chromatography. A Stable and Highly Precise Model for Hydrophobic Interactions in Biomembranes."

(43) Czarniecki, M. F.; Thornton, E. R. Biochem. Biophys. Res. Commun. 1977, 74, 553-558, "13C NMR Chemical Shift Titration of Metal Ion-Carbohydrate Complexes. An Unexpected Dichotomy for Ca+2 Binding Between Anomeric Derivatives of N-Acetylneuraminic Acid."

(42) Friedberger, M. P.; Thornton, E. R. J. Am. Chem. Soc. 1976, 98, 2861-2865, "Solvolysis Mechanisms. Sulfur Kinetic Isotope Effects in the Hydrolysis of Substituted Benzyldimethylsulfonium Tosylates."

(41) Tanaka, N.; Thornton, E. R. J. Am. Chem. Soc. 1976, 98, 1617-1619, "Isotope Effects in Hydrophobic Binding Measured by High-Pressure Liquid Chromatography."

(40) Huang, T. S.-C. C.; Thornton, E. R. J. Am. Chem. Soc. 1976, 98, 1542-1545, "Solvolysis Mechanisms. Kinetic Solvent Isotope Effects for Alkyl Tosylates in Acetic Acid and Acetic Acid-d."

(39) Czarniecki, M. F.; Thornton, E. R. J. Am. Chem. Soc. 1976, 98, 1023-1025, "13C Spin Lattice Relaxation in the Neuraminic Acids. Evidence for an Unusual Intramolecular Hydrogen Bonding Network."

(38) Winey, D. A.; Thornton, E. R. J. Am. Chem. Soc. 1975, 97, 3102-3108, "Elimination Mechanisms. Deuteroxide/Hydroxide Isotope Effects as a Measure of Proton Transfer in the Transition States for E2 Elimination of 2-(p-Trimethylammoniophenyl)ethyl 'Onium Ions and Halides. Mapping of the Reaction-Coordinate Motion."

(37) Wu, J. W.-T.; Thornton, E. R. J. Org. Chem. 1975, 40, 1041-1046, "The Effect of Phenyl Substitution at the Double Bond of Delta3-Cyclopentenylethyl p-Nitrobenzenesulfonate upon the Rate of Acetolysis to Norbornyl Products."

(36) Kim, J. H.; Thornton, E. R. J. Am. Chem. Soc. 1975, 97, 1865-1871, "Electrical Discharge Mechanisms. Stereochemistry of Electrocyclic Reactions of cis- and trans-1,2,3,4 Tetramethylcyclobutene and cis,cis,cis-, cis,cis,trans-, and trans,cis,trans-2,4,6-Octatriene. Hot Ground States as Probable Reactive Species."

(35) Palaitis, W.; Thornton, E. R. J. Am. Chem. Soc. 1975, 97, 1193-1196, "Kinetic Study of General and Specific Catalysis of Hydrolysis of Para-Substituted N-Benzoylimidazoles and of N-Acetylimidazole in Imidazole Buffers."

(34) Choi, M.-u.; Thornton, E. R. J. Am. Chem. Soc. 1974, 96, 1428-1436, "A Kinetic Study of the Hydrolysis of Substituted N-Benzoylimidazoles and N-Benzoyl--methylimidazolium Ions in Light and Heavy Water. Hydrogen Bridging without Rate-Determining Proton Transfer as a Mechanism of General Base Catalyzed Hydrolysis and a Model for Enzymic Charge-Relay."

(33) Taagepera, M.; Thornton, E. R. J. Am. Chem. Soc. 1972, 94, 1168-1177, "Secondary Deuterium Isotope Effects. The Transition State in the Reverse Diels-Alder Reaction of 9,10-Dihydro-9,10-ethanoanthracene. A Potentially General Method for Experimentally Determining Transition-State Symmetry and Distinguishing Concerted from Stepwise Mechanisms."

(32) Thornton, E. K.; Thornton, E. R. In Isotope Effects in Chemical Reactions; Collins, C. J.; Bowman, N. S., Eds.; Van Nostrand Reinhold: New York, 1970, Chapter 4, pp. 213-285, "Origin and Interpretation of Isotope Effects."

(31) Klinman, J. P.; Thornton, E. R. J. Am. Chem. Soc. 1968, 90, 4390-4394, "Solvolysis Mechanisms. A Kinetic Study of the Hydrolysis and Imidazole-Catalyzed Hydrolysis of p-Methyl-, p-Chloro-, and p-Nitrobenzoylimidazole in H2O and of p-Nitrobenzoylimidazole in D2O."

(30) Wang, B. J.-S.; Thornton, E. R. J. Am. Chem. Soc. 1968, 90, 1216-1224, "Mass Spectral Mechanisms. N-alkyl-3-cyano-1,4-dihydropyridine Fragmentation. Kinetic Isotope Effects for Expulsion of Deuterium from the 4 Position and Transition from Quantal to Purely Classical Isotope Effect."

(29) Frisone, G. J.; Thornton, E. R. J. Am. Chem. Soc. 1968, 90,1211-1215, "Solvolysis Mechanisms. beta-Deuterium Isotope Effects for t-Butyl Chloride Solvolysis at Constant Ionizing Power and Effect of Structure of Reactant on SN1 Transition State Geometry."

(28) Pentz, L.; Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 6931-6938, "Isotope Effects on the Basicity of 2-Nitrophenoxide, 2,4-Dinitrophenoxide, Hydroxide, and Imidazole in Protium Oxide-Deuterium Oxide Mixtures."

(27) Kaplan, E. D.; Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 6644-6651, "Secondary Deuterium Isotope Effects. beta-Kinetic Effects in SN2 Reactions of N,N-Dimethylaniline and Dimethylphenylphosphine with Methyl p-Toluenesulfonate and Comparison with Observed and Calculated Vibrational Frequencies of Deuterated and Undeuterated Dimethylaniline and Trimethylanilinium Ion."

(26) Steffa, L. J.; Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 6149-6156, "Elimination Mechanisms. Position of Proton and Substituent Effects Upon Geometry in E2 Transition States."

(25) Smith, E. P.; Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 5079-5080, "Mass Spectral Mechanisms. Preferential Association of Positive Charge with the Butadiene Fragment Containing the Vinyl Group of 4-Vinylcyclohexene in Competition with the Butadiene Fragment Arising from the Ring."

(24) Jones, T. C.; Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 4863-4867, "Solvolysis Mechanisms. SN1-Like Behavior of Methyl Chloromethyl Ether. Sensitivity to Solvent Ionizing Power and alpha-Deuterium Isotope Effect."

(23) Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 2915-2927, "A Simple Theory for Predicting the Effects of Substituent Changes on Transition-State Geometry."

(22) Weininger, S. J.; Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 2050-2054, "Probable Formation of Cyclobutadiene-Type Cations in the Mass-Spectral Decomposition of Pyridazines and Tetrazines."

(21) Thornton, E. R. Ann. Rev. Phys. Chem. 1966, 17, 349-372, Chapter on "Physical Organic Chemistry." [Review of Secondary Deuterium Isotope Effects]

(20) Callister, J. D.; Thornton, E. R. Nature 1965, 206, 504-505, "Electrical Discharge Mechanisms. Isoprene and Isoprene-d4."

(19) Weininger, S. J.; Mai, V. T.; Thornton, E. R. J. Am. Chem. Soc. 1964, 86, 3732-3735, "Mass Spectral Mechanisms. Homoallylic Participation in Fragmentation of Butadiene-Maleic Anhydride Adduct."

(18) Rothberg, I.; Thornton, E. R. J. Am. Chem. Soc. 1964, 86, 3302-3306, "Mechanisms of alpha-Elimination. p-Nitrobenzylsulfonium Ions Reacting with Aqueous Hydroxide."

(17) Rothberg, I.; Thornton, E. R. J. Am. Chem. Soc. 1964, 86, 3296-3301, "Mechanisms of alpha-Elimination. Nitrobenzylsulfonium, -ammonium, and -phosphonium Ions Reacting with Aqueous Hydroxide."

(16) Thornton, E. R. Solvolysis Mechanisms; The Ronald Press Co.: New York, 1964.

(15) Frisone, G. J.; Thornton, E. R. J. Am. Chem. Soc. 1964, 86, 1900-1901, "Isotope Effects for Solvolysis of t-Butyl Chloride and t-Butyl-d9 Chloride in Solvent Mixtures of Constant Ionizing Power."

(14) Steffa, L. J.; Thornton, E. R. J. Am. Chem. Soc. 1963, 85, 2680-2681, "Elimination Mechanisms. Position of Proton in E2 Transition States."

(13) Rothberg, I.; Thornton, E. R. J. Am. Chem. Soc. 1963, 85, 1704-1705, "Mechanisms of alpha-Elimination. Reactions of Nitrobenzyl 'Onium Ions with Aqueous Sodium Hydroxide."

(12) Thornton, E. R. J. Am. Chem. Soc. 1962, 84, 2474-2475, "Solvent Isotope Effects in H2O16 and H2O18."

(11) Thornton, E. R. J. Org. Chem. 1962, 27, 1943-1944, "Deductions from Small Primary Deuterium Isotope Effects."

(10) Singh, A.; Thornton, E. R.; Westheimer, F. H. J. Biol. Chem. 1962, 237, 3006-3008, "The Photolysis of Diazoacetylchymotrypsin."

(9) Swain, C. G.; Thornton, E. R. J. Am. Chem. Soc. 1962, 84, 822-826, "Initial-State and Transition-State Isotope Effects of Methyl Halides in Light and Heavy Water."

(8) Swain, C. G.; Thornton, E. R. J. Am. Chem. Soc. 1962, 84, 817-821, "Effect of Structural Changes in Reactants on the Structure of Transition States."

(7) Swain, C. G.; Thornton, E. R. J. Org. Chem. 1961, 26, 4808-4809, "Mechanism of Displacement by Hydroxide Ion on Benzylsulfonium Ions in Aqueous Solution."

(6) Swain, C. G.; Thornton, E. R. J. Am. Chem. Soc. 1961, 83, 4033-4034, "Mechanism of alpha-Elimination by Hydroxide Ion on p-Nitrobenzylsulfonium Ion in Aqueous Solution."

(5) Swain, C. G.; Thornton, E. R. J. Am. Chem. Soc. 1961, 83, 3890-3896, "Calculated Isotope Effects for Reactions of Lyoxide Ion or Water in Mixtures of Light and Heavy Water."

(4) Swain, C. G.; Thornton, E. R. J. Am. Chem. Soc. 1961, 83, 3884-3889, "Calculated Isotope Effects for Reactions of Lyonium Ion in Mixtures of Light and Heavy Water."

(3) Swain, C. G.; Thornton, E. R. Tetrahedron Lett. 1961, 2, 211-215, "Effect of Structural Changes in Reactants on the Structure of Transition States."

(2) Swain, C. G.; Bader, R. F. W.; Thornton, E. R. Tetrahedron 1960, 10, 200-211, "A Theoretical Interpretation of Isotope Effects in Mixtures of Light and Heavy Water."

(1) Thornton, E. R.; Stannett,.V.; Szwarc, M. J. Polymer Sci. 1958, 28,.465-468, "The Permeation of Vapors and Liquids through Polymer Films."


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