Simulations of adiabatic electrochemical reduction of the CF3I molecule - Assessment of different models

Journal of Chemical Theory and Computation

Volumn 9, Issue 10, 2013, Pages 4304-4312

  Ignaczak, Anna ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84885397022     PISSN: 15499618     EISSN: 15499626     Source Type: Journal    
DOI: 10.1021/ct400411v     Document Type: Article

References (72)

1. 3X (X=Cl, Br, I) Molecules Comput. Theor. Chem. 2011, 966, 340-351
2. Ignaczak, A. Solvent Effect on the Potential Energy Surfaces for the One-Electron Reduction of CF3X (X=Cl, Br, I) Molecules: A DFT PCM Study J. Phys. Chem. A 2012, 116, 11694-11701
3. Sibille, S.; Mcharek, S.; Périchon, J. Electrochemical Trifluoromethylation of Carbonyl Compounds Tetrahedron 1989, 45, 1423-1428
4. Vecchio-Sadus, A. M. The Electrochemical Synthesis of Inorganic and Organometallic Complexes in Non-Aqueous Media J. Appl. Electrochem. 1993, 23, 401-416
5. Aymard, F.; Nédélec, J.-Y.; Périchon, J. An Efficient Inexpensive Electrochemical Preparation of Ruppert's Reagent Tetrahedron Lett. 1994, 35, 8623-8624
6. Paratian, J. M.; Labbé, E.; Sibille, S.; Nédélec, J.-Y.; Périchon, J. Electrochemical Synthesis of Trifluoromethylcadmium and Trifluoromethylzinc Species Using Bromotrifluoromethane and Sacrificial anodes J. Organomet. Chem. 1995, 487, 61-64
7. Paratian, J. M.; Labbé, E.; Sibille, S.; Périchon, J. Electrosynthesis of (Trifluoromethyl)copper Complexes from Bromotrifluoromethane: Reactivities with Various Organic Halides J. Organomet. Chem. 1995, 489, 137-143
8. Fuchigami, T. Electrochemistry Applied to Synthesis of Fluorinated Organic Substances. In Advances In Electron Transfer Chemistry; Mariano, P., Ed.; JAI Press: Greenwich, CT, 1999; Vol. 6, pp 41-130.
9. Koshechko, V. G.; Kiprianova, L. A. Electrochemically Activated Insertion of Fluoroalkyl Groups into Organic and Inorganic Substrates Theor. Exp. Chem. 1999, 35, 18-36
10. Koshechko, V. G.; Pokhodenko, V. D. Electrochemical Activation of Freons Using Electron transfer Mediators Russ. Chem. Bull., Int. Ed. 2001, 50, 1929-1935
11. Singh, R. P.; Shreeve, J. M. Nucleophilic Trifluoromethylation Reactions of Organic Compounds with (Trifluoromethyl)trimethylsilane Tetrahedron 2000, 56, 7613-7632
12. Sonoyama, N.; Sakata, T. Electrochemical Hydrogenation of CFC-13 Using Metal-Supported Gas Diffusion Electrodes Environ. Sci. Technol. 1998, 32, 4005-4009
13. Sonoyama, N.; Sakata, T. Conversion of CFC-13 to Trifluoroacetic Acid by Electrochemical Reaction with Carbon Dioxide Chem. Lett. 2002, 31, 444-445
14. 3 Complexes Organometallics 2007, 26, 4152-4159
15. Ma, J.-A.; Cahard, D. Strategies for Nucleophilic, Electrophilic, and Radical trifluoromethylations J. Fluorine Chem. 2007, 128, 975-996
16. Grobe, J.; Hegge, J. Electrochemical and Chemical Syntheses of Trifluoromethylating Reagents and Trifluoromethyl Substituted Compounds Z. Anorg. Allg. Chem. 2008, 634, 1975-1990
17. 2n+1-I] 2000-2010 J. Fluorine Chem. 2012, 138, 3-23
18. Andrieux, C. P.; Savéant, J.-M.; Su, K.-B. Kinetics of Dissociative Electron Transfer. Direct and Mediated Electrochemical Reductive Cleavage of the Carbon-Halogen Bond J. Phys. Chem. 1986, 90, 3815-3823
19. Andrieux, C. P.; Gallado, I.; Savéant, J.-M.; Su, K.-B. Dissociative Electron Transfer. Homogeneous and Heterogeneous Reductive Cleavage of the Carbon-Halogen Bond in Simple Aliphatic Halides J. Am. Chem. Soc. 1986, 108, 638-647
20. Andrieux, C. P.; Gallado, I.; Savéant, J.-M. Outer-Sphere Electron-Transfer Reduction of Alkyl Halides. A Source of Alkyl Radicals or of Carbanions? Reduction of Alkyl Radicals J. Am. Chem. Soc. 1989, 111, 1620-1626
21. Andrieux, C. P.; Gélis, L.; Médebielle, M.; Pinson, J.; Savéant, J.-M. Outer-Sphere Dissociative Electron Transfer to Organic Molecules: A Source of Radicals or Carbanions? Direct and Indirect Electrochemistry of Perfluoroalkyl Bromides and Iodides J. Am. Chem. Soc. 1990, 112, 3509-3520
22. Médebielle, M.; Pinson, J.; Savéant, J.-M. Electrochemically Induced Nucleophilic Substitution of Perfluoroalkyl Halides. An Example of a Dissociative Electron-Transfer-Induced Chemical Reaction J. Am. Chem. Soc. 1991, 113, 6872-6879
23. Médebielle, M.; Pinson, J.; Savéant, J.-M. Electrochemically Induced Nucleophilic Substitution of Perfluoroalkyl Halides: an Example of a Dissociative Electron-Transfer-Induced Chemical Reaction J. Fluorine Chem. 1992, 58, 254
24. Bertran, J.; Gallardo, I.; Moreno, M.; Savéant, J.-M. Dissociative Electron Transfer. Ab Initio Study of the Carbon-Halogen Bond Reductive Cleavage in Methyl and Perfluoromethyl Halides. Role of the Solvent J. Am. Chem. Soc. 1992, 114, 9576-9583
25. Andrieux, C. P.; Le Gorande, A.; Savéant, J.-M. Electron Transfer and Bond Breaking. Examples of Passage from a Sequential to a Concerted Mechanism in the Electrochemical Reductive Cleavage of Arylmethyl Halides J. Am. Chem. Soc. 1992, 114, 6892-6904
26. Andrieux, C. P.; Savéant, J.-M.; Tardy, C. Cage and Entropy Effects in the Dynamics of Dissociative Electron Transfer J. Am. Chem. Soc. 1998, 120, 4167-4175
27. Costentin, C.; Robert, M.; Savéant, J.-M. Successive Removal of Chloride Ions from Organic Polychloride Pollutants. Mechanisms of Reductive Electrochemical Elimination in Aliphatic Gem-Polychlorides, α,β- Polychloroalkenes, and α,β-Polychloroalkanes in Mildly Protic Medium J. Am. Chem. Soc. 2003, 125, 10729-20739
28. Rozhkov, I.; Becker, G.; Igumnov, S.; Pletnev, S.; Rempel, G.; Borisov, Y. Reduction Potential and Relative Electron Affinity As reactivity Indexes of Perfluoroalkyl Halides J. Fluorine Chem. 1989, 45, 114
29. Volodin, Yu. Yu.; Stepanov, A. A.; Denisovich, L. I.; Grinberg, V. A. Electrocatalytic Reduction of Trifluoroiodomethane in the Presence of Cobaloximes Russ. J. Electrochem. 2000, 36, 1026-1028
30. 3 Chem. Phys. 1999, 244, 439-448
31. Batanov, G. M.; Kossyi, I. A.; Silakov, V. P. Gas-Discharge Method for Improving the Environmental Characteristics of the Atmosphere (In memory of G.A. Askar'yan) Plasma Phys. Rep. 2002, 28, 204-228
32. 3Cl Attachment Rate Constants up to 1100 K J. Chem. Phys. 2009, 131, 84302
33. 3Cl Inelastic Scattering J. Phys. B 1999, 32, 663-673
34. Fabrikant, I. I.; Hotop, H. On the Validity of the Arrhenius Equation for Electron Attachment Rate Coefficients J. Chem. Phys. 2008, 128, 124308
35. 3Ī Radical Anions J. Chem. Phys. 1997, 106, 7709-7713
36. Roszak, S.; Koski, W. S.; Kaufman, J. J.; Balasubramanian, K. Structure and Electron Attachment Properties of Halomethanes (CXnYm, X=H, F; Y=Cl, Br, I; n=0,4; m=4-n) SAR QSAR Environ. Res. 2000, 14, 1-15
37. Berry, R. J.; Burgess, D. R. F., Jr.; Nyden, M. R.; Zachariah, M. R.; Melis, C. F.; Schwartz, M. Halon Thermochemistry: Calculated Enthalpies of Formation of Chlorofluoromethanes J. Phys. Chem. 1996, 100, 7405-7410
38. Luke, B. T.; Loew, G. H.; McLean, A. D. Theoretical Investigation of the Anaerobic Reduction of Halogenated Alkanes by Cytochrome P-450. 2. Vertical Electron Affinities of Chlorofluoromethanes as a Measure Their Activity J. Am. Chem. Soc. 1988, 110, 3396-3400
39. m series, n+m=3 and 4 J. Chem. Phys. 1993, 98, 7072-7080
40. 3Cl Chem. Phys. 2000, 255, 1-14
41. 2, SH, Cl) Z. Anorg. Allg. Chem. 2007, 633, 2678-2682
42. Rempel, G. D.; Borisov, Yu.A.; Raevskii, N. I.; Igumnov, S. M.; Rozhkov, I. N. Electron Structure and Reactivity of Organofluorine Compounds. 3. MNDO and AM1 Calculations of the Ground State of Perfluoroalkyl Chlorides, Bromides, and Iodides Russ. Chem. Bull. 1990, 39, 947-950
43. Rempel, G. D.; Borisov, Yu.A.; Raevskii, N. I.; Igumnov, S. M.; Rozhkov, I. N. Electron Structure and Reactivity of Organofluorine Compounds. 4. AM1 Calculations of Anion Radicals of Primary, Secondary, and Tertiary Perfluoroalkyl Chlorides, Bromides, and Iodides Russ. Chem. Bull. 1990, 39, 951-955
44. 3I J. Phys. B 2003, 36, 1263-1272
45. Abraham, R. J.; Griffith, L.; Loftus, P. Approaches to Charge Calculations in Molecular Mechanics J. Comput. Chem. 1982, 3, 407-416
46. Abraham, R. J.; Grant, G. H. Charge Calculations in Molecular Mechanics. IX. A General Parameterisation of the Scheme for Saturated Halogen, Oxygen and Nitrogen Compounds J. Comput.-Aided Mol. Des. 1992, 6, 273-286
47. Pezler, B.; Szamrej, I. Geometry and energy changes in halomethanes due to electron capture Res. Chem. Intermed. 2001, 27, 787-794
48. Senthilkumar, K.; Kolandaivel, P. Hartree-Fock and Density Functional Theory Studies on Ionization and Fragmentation of Halomethane Molecules by Positron Impact Mol. Phys. 2002, 100, 3817-3822
49. Preston, H. J. T.; Kaufman, J. J. MS Xα Calculations on the Chlorofluoromethanes Chem. Phys. Lett. 1977, 50, 157-161
50. 3 J. Fluorine Chem. 2001, 108, 177-186
51. German, E. D.; Tikhomirov, V. A. A Semiempirical Study of Radical Anions CY3X̄ (Y=H, F, Cl and Br, X=Cl and Br) J. Mol. Struct.: THEOCHEM 1998, 423, 251-261
52. 3X (Y-=H, F, Cl and Br; X=Cl and Br) in solvent: a semiempirical PM3 method Study J. Electroanal. Chem. 1998, 450, 13-20
53. Ignaczak, A.; Schmickler, W. Theoretical Study of a Non-Adiabatic Dissociative Electron Transfer Reaction J. Electroanal. Chem. 2003, 554-555, 201-209
54. Ignaczak, A.; Schmickler, W. MD Simulations of Heterogeneous Reduction of the Tert-Butyl Bromide Molecule Electrochim. Acta 2010, 55, 2442-2450
55. Ignaczak, A. Electrochemical Reduction of Tert-Butyl Chloride- Computational Study Electrochim. Acta 2010, 55, 3650-3656
56. Ignaczak, A. Comparison of Temperature Effect on Electroreduction of Tert-Butyl Chloride and Tert-Butyl Bromide-Theoretical Study Electrochim. Acta 2011, 56, 6305-6311
57. Koper, M. T. M.; Voth, G. A. A Theory of Adiabatic Bond Breaking Electron Transfer Reactions at Metal Electrodes Chem. Phys. Lett. 1998, 282, 100-106
58. Schmickler, W.; Koper, M. T. M. Adiabatic Electrochemical Electron-Transfer Reactions Involving Frequency Changes of Inner-Sphere Modes Electrochem. Commun. 1999, 1, 402-405
59. Kast, S. M.; Nicklas, K.; Bär, H.-J.; Brickmann, J. Constant Temperature Molecular Dynamics Dimulations by Means of a Stochastic Collision Model. I. Noninteracting Particles J. Chem. Phys. 1994, 100, 566-576
60. Kast, S. M.; Brickmann, J. Constant Temperature Molecular Dynamics Simulations by Means of a Stochastic Collision Model. II. The Harmonic Oscillator J. Chem. Phys. 1996, 104, 3732-3741
61. Ignaczak, A.; Schmickler, W. Effects of Friction and Asymmetric Inner Sphere Reorganization Energy on the Electron Transfer Reaction Rate-Two-Dimensional Simulations Electrochim. Acta 2007, 52, 5621-5633
62. Ignaczak, A. Adiabatic Versus Non-Adiabatic Approach to the Inner Sphere Vibrational Effects on Electrochemical Reduction Rates Electrochim. Acta 2008, 53, 2619-2629
63. Whitnell, R. M.; Wilson, K. R.; Hynes, J. T. Vibrational Relaxation of a Dipolar Molecule in Water J. Chem. Phys. 1992, 96, 5354-5369
64. Murarka, R. K.; Bhattacharyya, S.; Biswas, R.; Bagchi, B. Isomerization Dynamics in Viscous Liquids: Microscopic Investigation of the Coupling and Decoupling of the Rate to and from Solvent Viscosity and Dependence on the Intermolecular Potential J. Chem. Phys. 1999, 110, 7365-7375
65. Bagchi, A.; Srinivas, G.; Miyazaki, K. The Enskog Theory for Classical Vibrational Energy Relaxation in Fluids with Continuous Potentials J. Chem. Phys. 2001, 115, 4195-4198
66. Northrup, S. H.; McCammon, J. A. Saddle-Point Avoidance in Diffusional Reactions J. Chem. Phys. 1983, 78, 987-989
67. Berkowitz, M.; Morgan, J. D.; McCammon, J. A.; Northrup, S. H. Diffusion-Controlled Reactions: A Variational Formula for the Optimum Reaction Coordinate J. Chem. Phys. 1983, 79, 5563-5565
68. Larson, R. S. Simulation of Two-Dimensional Diffusive Barrier Crossing with a Curved Reaction Path Physica A 1986, 137, 295-305
69. Berezhkovskii, A. M.; Berezhkovskii, L. M.; Zitserman, V. Yu. The Rate Constant in the Kramers Multidimensional Theory and the Saddle-Point Avoidance Chem. Phys. 1989, 130, 55-63
70. Berezhkovskii, A. M.; Zitserman, V. Yu.; Sheu, S.-Y.; Yang, D.-Y.; Kuo, J.; Lin, S. H. Kramers Theory of Chemical Reactions in a Slowly Adjusting Environment J. Chem. Phys. 1997, 107, 10539-10554
71. Savéant, J.-M. A Simple Model for the Kinetics of Dissociative Electron Transfer in Polar Solvents. Application to the Homogeneous and Heterogeneous Reduction of Alkyl Halides J. Am. Chem. Soc. 1987, 109, 6788-6795
72. Savéant, J.-M. Dissociative Electron Transfer. New Tests of the Theory in the Electrochemical and Homogeneous Reduction of Alkyl Halides J. Am. Chem. Soc. 1992, 114, 10595-10602