Transition-State Structure for the Quintessential SN2 Reaction of a Carbohydrate: Reaction of α-Glucopyranosyl Fluoride with Azide Ion in Water

Jefferson Chan; Natalia Sannikova; Ariel Tang; Andrew J. Bennet

doi:10.1021/ja506092h

Transition-State Structure for the Quintessential SN2 Reaction of a Carbohydrate: Reaction of α-Glucopyranosyl Fluoride with Azide Ion in Water

Journal of the American Chemical Society ◽

10.1021/ja506092h ◽

2014 ◽

Vol 136 (35) ◽

pp. 12225-12228 ◽

Cited By ~ 19

Author(s):

Jefferson Chan ◽

Natalia Sannikova ◽

Ariel Tang ◽

Andrew J. Bennet

Keyword(s):

Transition State ◽

State Structure ◽

Transition State Structure ◽

Sn2 Reaction ◽

Azide Ion

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ChemInform Abstract: REACTIVITY-SELECTIVITY RELATIONSHIPS. A QUANTUM-MECHANICAL APPROACH TO TRANSITION-STATE STRUCTURE. APPLICATION TO THE SN2 REACTION OF BENZYL DERIVATIVES

Chemischer Informationsdienst ◽

10.1002/chin.198140063 ◽

1981 ◽

Vol 12 (40) ◽

Author(s):

A. PROSS ◽

S. S. SHAIK

Keyword(s):

Transition State ◽

Quantum Mechanical ◽

State Structure ◽

Transition State Structure ◽

Sn2 Reaction ◽

Mechanical Approach ◽

Quantum Mechanical Approach

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Reactivity-selectivity relationships. A quantum-mechanical approach to transition-state structure. Application to the SN2 reaction of benzyl derivatives

Journal of the American Chemical Society ◽

10.1021/ja00403a015 ◽

1981 ◽

Vol 103 (13) ◽

pp. 3702-3709 ◽

Cited By ~ 50

Author(s):

Addy Pross ◽

Sason S. Shaik

Keyword(s):

Transition State ◽

Quantum Mechanical ◽

State Structure ◽

Transition State Structure ◽

Sn2 Reaction ◽

Mechanical Approach ◽

Quantum Mechanical Approach

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Experimental and Theoretical Multiple Kinetic Isotope Effects for an SN2 Reaction. An Attempt to Determine Transition-State Structure and the Ability of Theoretical Methods to Predict Experimental Kinetic Isotope Effects

Chemistry - A European Journal ◽

10.1002/chem.200204119 ◽

2003 ◽

Vol 9 (12) ◽

pp. 2696-2709 ◽

Cited By ~ 29

Author(s):

Yao-ren Fang ◽

Ying Gao ◽

Per Ryberg ◽

Jonas Eriksson ◽

Magdalena Kołodziejska-Huben ◽

...

Keyword(s):

Transition State ◽

Isotope Effects ◽

Kinetic Isotope Effects ◽

State Structure ◽

Transition State Structure ◽

Theoretical Methods ◽

Kinetic Isotope ◽

Sn2 Reaction

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ChemInform Abstract: Temperature Dependence of the Transition-State Structure for the Disproportionation of Hydrogen Atom with Ethyl Radical.

Chemischer Informationsdienst ◽

10.1002/chin.198603102 ◽

1986 ◽

Vol 17 (3) ◽

Author(s):

C. JUN. DOUBLEDAY ◽

J. MCIVER ◽

M. PAGE ◽

T. ZIELINSKI

Keyword(s):

Hydrogen Atom ◽

Transition State ◽

Temperature Dependence ◽

State Structure ◽

Transition State Structure ◽

Ethyl Radical

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ChemInform Abstract: INFLUENCE OF THE STERIC REQUIREMENTS OF THE NUCLEOPHILE ON THE TRANSITION STATE STRUCTURE OF E2 REACTIONS. A KINETIC STUDY OF THE ELIMINATIONS FROM 1-BROMO-2-ARYLETHANES AND 1-CHLORO-1-PHENYL-2-ARYLETHANES PROMOTED BY SODIUM 2,6-DI-TE

Chemischer Informationsdienst ◽

10.1002/chin.197843071 ◽

1978 ◽

Vol 9 (43) ◽

Author(s):

S. ALUNNI ◽

E. BACIOCCHI ◽

P. PERUCCI ◽

R. RUZZICONI

Keyword(s):

Transition State ◽

Kinetic Study ◽

State Structure ◽

Transition State Structure

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A Semiempirical Transition State Structure for the First Step in the Alkaline Hydrolysis of Cocaine. Comparison between the Transition State Structure, the Phosphonate Monoester Transition State Analog, and a Newly Designed Thiophosphonate Transition State Analog

Journal of Molecular Modeling ◽

10.1007/s0089460020062 ◽

1996 ◽

Vol 2 (3-4) ◽

pp. 62-69 ◽

Cited By ~ 12

Author(s):

Edward C. Sherer ◽

Gordon M. Turner ◽

Tricia N. Lively ◽

Donald W. Landry ◽

George C. Shields

Keyword(s):

Transition State ◽

Alkaline Hydrolysis ◽

State Structure ◽

Transition State Structure ◽

Transition State Analog ◽

Hydrolysis Of

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Rearrangement of chorismate to prephenate. Use of chorismate mutase inhibitors to define the transition state structure

Biochemistry ◽

10.1021/bi00641a015 ◽

1977 ◽

Vol 16 (22) ◽

pp. 4848-4852 ◽

Cited By ~ 44

Author(s):

P. R. Andrews ◽

E. N. Cain ◽

E. Rizzardo ◽

G. D. Smith

Keyword(s):

Transition State ◽

Chorismate Mutase ◽

State Structure ◽

Transition State Structure

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Conservation of Transition State Structure in Fast Folding Peripheral Subunit-Binding Domains

Journal of Molecular Biology ◽

10.1016/j.jmb.2008.06.081 ◽

2008 ◽

Vol 383 (1) ◽

pp. 224-237 ◽

Cited By ~ 17

Author(s):

Timothy D. Sharpe ◽

Neil Ferguson ◽

Christopher M. Johnson ◽

Alan R. Fersht

Keyword(s):

Transition State ◽

State Structure ◽

Transition State Structure ◽

Binding Domains

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Transition-state structure as a unifying basis in protein-folding mechanisms: Contact order, chain topology, stability, and the extended nucleus mechanism

Proceedings of the National Academy of Sciences ◽

10.1073/pnas.97.4.1525 ◽

2000 ◽

Vol 97 (4) ◽

pp. 1525-1529 ◽

Cited By ~ 235

Author(s):

A. R. Fersht

Keyword(s):

Protein Folding ◽

Transition State ◽

State Structure ◽

Transition State Structure ◽

Contact Order

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Cross interaction constants as a measure of transition state structure. Part 7. Aminolysis of alkyl benzenesulphonates

Journal of the Chemical Society Perkin Transactions 2 ◽

10.1039/p29890001881 ◽

1989 ◽

pp. 1881 ◽

Cited By ~ 9

Author(s):

Ikchoon Lee ◽

Young Hoon Choi ◽

Keun Woo Rhyu ◽

Chang Sub Shim

Keyword(s):

Transition State ◽

State Structure ◽

Transition State Structure

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