Hierarchy of relative bond dissociation enthalpies and their use to efficiently compute accurate absolute bond dissociation enthalpies for C-H, C-C, and C-F bonds

Journal of Physical Chemistry A

Volumn 117, Issue 17, 2013, Pages 3666-3675

  Chan, Bun ^a   Radom, Leo ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVITY; APPROXIMATION METHODS; BOND DISSOCIATION ENTHALPIES; ELECTRON-DONATING GROUP; ELECTRONWITHDRAWING; HYBRID DFT; HYBRID DFT METHOD; QUANTUM CHEMISTRY METHODS;

QUANTUM CHEMISTRY;

CHEMICAL BONDS;

EID: 84877027495     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp401248r     Document Type: Article

References (54)

1. Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements, 2 nd ed.; Butterworth-Heinemann: Burlington, 1997.
2. Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry; Oxford University Press: Oxford, 2001.
3. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5 th ed.; John Wiley and Sons: New York, 2001.
4. Brown, T. L.; LeMay, Jr., H. E.; Bursten, B. E.; Murphy, C. J. Chemistry: The Central Science, 11 th ed.; Pearson Education: Upper Saddle River, NJ, 2009.
5. For a comprehensive compilation of experimental BDEs, see: Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007.
6. Martin, J. M. L. Computational Thermochemistry: A Brief Overview of Quantum Mechanical Approaches Ann. Rep. Comput. Chem. 2005, 1, 31-43
7. Fabian, W. M. F. Accurate Thermochemistry from Quantum Chemical Calculations? Monat. Chem. 2008, 139, 309-318
8. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. G n Theory WIREs: Comput. Mol. Sci. 2011, 1, 810-825
9. Peterson, K. A.; Feller, D.; Dixon, D. A. Chemical Accuracy in Ab Initio Thermochemistry and Spectroscopy: Current Strategies and Future Challenges Theor. Chem. Acc. 2012, 131, 1079-1-20
10. Zipse, H. Radical Stability-A Theoretical Perspective Top. Curr. Chem. 2006, 263, 163-189
11. Coote, M. L.; Lin, C.-Y.; Zipse, H. The Stability of Carbon-Centered Radicals. In Carbon-Centered Free Radicals and Radical Cations: Structure, Reactivity and Dynamics; Forbes, M. D. E., Ed.; John Wiley & Sons: New York, 2010; pp 83-104.
12. Hioe, J.; Zipse, H. Radical Stability-Thermochemical Aspects. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A., Ed., John Wiley & Sons: Chichester, U.K., 2012, pp 449-476.
13. Coote, M. L.; Lin, C. Y.; Beckwith, A. L.; Zavitsas, A. A. A Comparison of Methods for Measuring Relative Radical Stabilities of Carbon-Centred Radicals Phys. Chem. Chem. Phys. 2010, 12, 9597-9610
14. Chan, B.; Radom, L. BDE261: A Comprehensive Set of High-Level Theoretical Bond Dissociation Enthalpies J. Phys. Chem. A 2012, 116, 4975-4986 and references therein.
15. Menon, A. S.; Henry, D. J.; Bally, T.; Radom, L. Effect of Substituents on the Stabilities of Multiply-Substituted Carbon-Centered Radicals Org. Biomol. Chem. 2011, 9, 3636-3657 and reference therein.
16. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. Gaussian-2 Theory for Molecular Energies of First- and Second-Row Compounds J. Chem. Phys. 1991, 94, 7221-7230
17. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. Gaussian-3 (G3) Theory for Molecules Containing First and Second-Row Atoms J. Chem. Phys. 1998, 109, 7764-7776
18. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-4 Theory J. Chem. Phys. 2007, 126, 084108-1-12
19. See for example: Schwabe, T.; Grimme, S. Theoretical Thermodynamics for Large Molecules: Walking the Thin Line between Accuracy and Computational Cost Acc. Chem. Res. 2008, 41, 569-579
20. For an overview on density functional theory see: Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2 nd ed.; Wiley: New York, 2001.
21. Chan, B.; Deng, J.; Radom, L. G4(MP2)-6X: A Cost-Effective Improvement to G4(MP2) J. Chem. Theory Comput. 2011, 7, 112-120
22. Chan, B.; Radom, L. Obtaining Good Performance with Triple-ζ-Type Basis Sets in Double-Hybrid Density Functional Theory Procedures J. Chem. Theory Comput. 2011, 7, 2852-2863
23. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals Theor. Chem. Acc. 2008, 120, 215-241
24. Dapprich, S.; Komáromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. A New ONIOM Implementation in Gaussian 98. Part 1. The Calculation of Energies, Gradients and Vibrational Frequencies and Electric Field Derivatives J. Mol. Struct. THEOCHEM 1991, 462, 1-21
25. Izgorodina, E. I.; Brittain, D. R. B.; Hodgson, J. L.; Krenske, E. H.; Lin, C. Y.; Namazian, M.; Coote, M. L. Should Contemporary Density Functional Theory Methods be Used to Study the Thermodynamics of Radical Reactions? J. Phys. Chem. A 2007, 111, 10754-10768
26. Wheeler, S. E.; Houk, K. N.; Schleyer, P. v. R.; Allen, W. D. A Hierarchy of Homodesmotic Reactions for Thermochemistry J. Am. Chem. Soc. 2009, 131, 2547-2560
27. Wodrich, M. D.; Corminboeuf, C.; Wheeler, S. E. Accurate Thermochemistry of Hydrocarbon Radicals via an Extended Generalized Bond Separation Reaction Scheme J. Phys. Chem. A 2012, 116, 3436-3447
28. Ramabhadran, R. O.; Raghavachari, K. Theoretical Thermochemistry for Organic Molecules: Development of the Generalized Connectivity-Based Hierarchy J. Chem. Theory Comput. 2011, 7, 2094-2103
29. Ramabhadran, R. O.; Raghavachari, K. Connectivity-Based Hierarchy for Theoretical Thermochemistry: Assessment Using Wave Function-Based Methods J. Phys. Chem. A 2012, 116, 7531-7537
30. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
31. Jensen, F. Introduction to Computational Chemistry, 2 nd ed.; Wiley: Chichester, U.K., 2007.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
33. Werner, H.-J.; Knowles, P. J.; Manby, F. R.; Schütz, M.; Celani, P.; Knizia, G.; Korona, T.; Lindh, R.; Mitrushenkov, A.; Rauhut, G.; MOLPRO 2010.1; University College Cardiff Consultants Limited: Cardiff, U.K., 2010.
34. Chan, B.; Radom, L. W1X-1 and W1X-2: W1-Quality Accuracy with an Order of Magnitude Reduction in Computational Cost J. Chem. Theory Comput. 2012, 8, 4259
35. Martin, J. M. L.; De Oliveira, G. Towards Standard Methods For Benchmark Quality Ab Initio Thermochemistry-W1 And W2 Theory J. Chem. Phys. 1999, 111, 1843-1856
36. Johnson, B. G.; Gill, P. M. W.; Pople, J. A. The Performance of a Family of Density Functional Methods J. Chem. Phys. 1993, 98, 5612-5626
37. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
38. Becke, A. D. Density-Functional Thermochemistry. IV. A New Dynamical Correlation Functional and Implications for Exact-Exchange Mixing J. Chem. Phys. 1996, 104, 1040-1046
39. Zhao, Y.; Truhlar, D. G. A New Local Density Functional for Main-Group Thermochemistry, Transition Metal Bonding, Thermochemical Kinetics, and Noncovalent Interactions J. Chem. Phys. 2006, 125, 194101-1-18
40. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
41. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods Without Adjustable Parameters: The PBE0Model J. Chem. Phys. 1999, 110, 6158-6170
42. Schmider, H. L.; Becke, A. D. Optimized Density Functionals from the Extended G2 Test Set J. Chem. Phys. 1998, 108, 9624-9631
43. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132, 154104-1-19
44. Yanai, T.; Tew, D.; Handy, N. A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP) Chem. Phys. Lett. 2004, 393, 51-57
45. Vydrov, O. A.; Scuseria, G. E. Assessment of a Long-Range Corrected Hybrid Functional J. Chem. Phys. 2006, 125, 234109-1-9
46. Chai, J.-D.; Head-Gordon, M. Systematic Optimization of Long-Range Corrected Hybrid Density Functionals J. Chem. Phys. 2008, 128, 084106-1-15
47. Becke, A. D.; Johnson, E. A Density-Functional Model of the Dispersion Interaction J. Chem. Phys. 2005, 122, 154101-1-9
48. Grimme, S.; Ehrlich, S.; Goerigk, L. Effect of the Damping Function in Dispersion Corrected Density Functional Theory J. Comput. Chem. 2011, 32, 1456-1465
49. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. A Complete Basis Set Model Chemistry. VI. Use of Density Functional Geometries and Frequencies J. Chem. Phys. 1999, 110, 2822-2827
50. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. A Complete Basis Set Model Chemistry. VII. Use of the Minimum Population Localization Method J. Chem. Phys. 2000, 112, 6532-6542
51. Henry, D. J.; Sullivan, M. B.; Radom, L. G3-RAD and G3X-RAD: Modified Gaussian-3 (G3) and Gaussian-3X (G3X) Procedures for Radical Thermochemistry J. Chem. Phys. 2003, 118, 4849-4860
52. Graham, D. C.; Menon, A. S.; Goerigk, L.; Grimme, S.; Radom, L. Optimization and Basis-Set Dependence of a Restricted-Open-Shell Form of B2-PLYP Double-Hybrid Density Functional Theory J. Phys. Chem. A 2009, 113, 9861-9873
53. Viehe, H. G.; Merenyi, R.; Stella, L.; Janousek, Z. Captodative Substituent Effects in Syntheses with Radicals and Radicophiles Angew. Chem., Int. Ed. Engl. 1979, 18, 917-932
54. Viehe, H. G.; Merenyi, R.; Janousek, Z. Captodative Substituent Effects in Radical Chemistry Pure Appl. Chem. 1988, 60, 1635-1644