A Single Transition State Serves Two Mechanisms: An ab Initio Classical Trajectory Study of the Electron Transfer and Substitution Mechanisms in Reactions of Ketyl Radical Anions with Alkyl Halides

Vebjørn Bakken; David Danovich; Sason Shaik; H. Bernhard Schlegel

doi:10.1021/ja002799k

A Single Transition State Serves Two Mechanisms: An ab Initio Classical Trajectory Study of the Electron Transfer and Substitution Mechanisms in Reactions of Ketyl Radical Anions with Alkyl Halides

Journal of the American Chemical Society ◽

10.1021/ja002799k ◽

2001 ◽

Vol 123 (1) ◽

pp. 130-134 ◽

Cited By ~ 43

Author(s):

Vebjørn Bakken ◽

David Danovich ◽

Sason Shaik ◽

H. Bernhard Schlegel

Keyword(s):

Electron Transfer ◽

Transition State ◽

Ab Initio ◽

Classical Trajectory ◽

Alkyl Halides ◽

Radical Anions ◽

Ketyl Radical ◽

Single Transition

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Single Transition State Serves Two Mechanisms. Ab Initio Classical Trajectory Calculations of the Substitution−Electron Transfer Branching Ratio in CH2O•-+ CH3Cl

The Journal of Physical Chemistry A ◽

10.1021/jp046827n ◽

2004 ◽

Vol 108 (40) ◽

pp. 8526-8532 ◽

Cited By ~ 22

Author(s):

Jie Li ◽

Xiaosong Li ◽

Sason Shaik ◽

H. Bernhard Schlegel

Keyword(s):

Electron Transfer ◽

Transition State ◽

Ab Initio ◽

Branching Ratio ◽

Classical Trajectory ◽

Trajectory Calculations ◽

Single Transition

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Towards the Definition of the Maximum Allowable Tightness of an Electron Transfer Transition State in the Reactions of Radical Anions and Alkyl Halides

Angewandte Chemie International Edition in English ◽

10.1002/anie.199610981 ◽

1996 ◽

Vol 35 (10) ◽

pp. 1098-1100 ◽

Cited By ~ 15

Author(s):

G. Narahari Sastry ◽

David Danovich ◽

Sason Shaik

Keyword(s):

Electron Transfer ◽

Transition State ◽

Alkyl Halides ◽

Radical Anions ◽

Definition Of

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Ab initio molecular dynamics studies on substitution vs electron transfer reactions of substituted ketyl radical anions with chloroalkanes: how do the two products form in a borderline mechanism?

Journal of Physical Organic Chemistry ◽

10.1002/poc.610 ◽

2003 ◽

Vol 16 (8) ◽

pp. 475-483 ◽

Cited By ~ 15

Author(s):

Hiroshi Yamataka ◽

Misako Aida ◽

Michel Dupuis

Keyword(s):

Molecular Dynamics ◽

Electron Transfer ◽

Ab Initio ◽

Transfer Reactions ◽

Ab Initio Molecular Dynamics ◽

Radical Anions ◽

Ketyl Radical ◽

Electron Transfer Reactions

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Dissociative Electron Transfer, Substitution, and Borderline Mechanisms in Reactions of Ketyl Radical Anions. Differences and Difficulties in Their Reaction Paths

Journal of the American Chemical Society ◽

10.1021/ja971105d ◽

1997 ◽

Vol 119 (39) ◽

pp. 9237-9245 ◽

Cited By ~ 28

Author(s):

Sason Shaik ◽

David Danovich ◽

G. Narahari Sastry ◽

Philippe Y. Ayala ◽

H. Bernhard Schlegel

Keyword(s):

Electron Transfer ◽

Radical Anions ◽

Reaction Paths ◽

Ketyl Radical ◽

Dissociative Electron Transfer

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ChemInform Abstract: Stereoelectronic Effects in Intramolecular Long-Distance Electron Transfer in Radical Anions as Predicted by ab initio MO Calculations

Chemischer Informationsdienst ◽

10.1002/chin.198628158 ◽

1986 ◽

Vol 17 (28) ◽

Author(s):

K. OHTA ◽

G. L. CLOSS ◽

K. MOROKUMA ◽

N. J. GREEN

Keyword(s):

Electron Transfer ◽

Ab Initio ◽

Radical Anions ◽

Mo Calculations ◽

Long Distance ◽

Stereoelectronic Effects ◽

Ab Initio Mo Calculations ◽

Ab Initio Mo

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Kinetics of electron transfer from aromatic radical anions to alkyl halides in tetrahydrofuran. Effects of sodium cation pairing

The Journal of Physical Chemistry ◽

10.1021/j100640a008 ◽

1973 ◽

Vol 77 (22) ◽

pp. 2618-2622 ◽

Cited By ~ 12

Author(s):

Bradley Bockrath ◽

Leon M. Dorfman

Keyword(s):

Electron Transfer ◽

Sodium Cation ◽

Alkyl Halides ◽

Radical Anions ◽

Aromatic Radical ◽

Kinetics Of

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Structured Electron Transfer Transition State. Valence Bond Configuration Mixing Analysis and ab Initio Calculations of the Reactions of Formaldehyde Radical Anion with Methyl Chloride

The Journal of Physical Chemistry ◽

10.1021/jp952827z ◽

1996 ◽

Vol 100 (30) ◽

pp. 12241-12252 ◽

Cited By ~ 30

Author(s):

G. Narahari Sastry ◽

Sason Shaik

Keyword(s):

Electron Transfer ◽

Transition State ◽

Ab Initio Calculations ◽

Ab Initio ◽

Radical Anion ◽

Valence Bond ◽

Methyl Chloride ◽

Configuration Mixing

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Generation of ketyl radical anions by photoinduced electron transfer (PET) between ketones and amines. Synthetic applications

Tetrahedron ◽

10.1016/j.tet.2006.03.062 ◽

2006 ◽

Vol 62 (27) ◽

pp. 6459-6470 ◽

Cited By ~ 51

Author(s):

Janine Cossy ◽

Damien Belotti

Keyword(s):

Electron Transfer ◽

Photoinduced Electron Transfer ◽

Radical Anions ◽

Ketyl Radical

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Competitive Electron Transfer and SN2 Reactions of Aromatic Radical Anions with Alkyl Halides and Methanesulfonates.

Acta Chemica Scandinavica ◽

10.3891/acta.chem.scand.52-0051 ◽

1998 ◽

Vol 52 ◽

pp. 51-61 ◽

Cited By ~ 12

Author(s):

Heidi Skovbak Sørensen ◽

Kim Daasbjerg ◽

Lennart Eberson ◽

Björn Åkermark ◽

John H. Wagenknecht ◽

...

Keyword(s):

Electron Transfer ◽

Alkyl Halides ◽

Radical Anions ◽

Aromatic Radical ◽

Sn2 Reactions

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Evidence for electron transfer in reactions of nucleophiles with optically active alkyl halides. A challenge to the SN2 transition state.

Tetrahedron Letters ◽

10.1016/s0040-4039(00)95466-2 ◽

1987 ◽

Vol 28 (28) ◽

pp. 3183-3186 ◽

Cited By ~ 10

Author(s):

E.C Ashby ◽

Tung N Pham

Keyword(s):

Electron Transfer ◽

Transition State ◽

Optically Active ◽

Alkyl Halides

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