Heterogeneous substitution effects in chlorocyanomethyl radical and chlorocyanocarbene

Journal of Physical Chemistry A

Volumn 117, Issue 41, 2013, Pages 10681-10691

  Khuseynov, Dmitry ^a   Dixon, Andrew R ^a   Goebbert, Daniel J ^a,b   Sanov, Andrei ^a  

^a The University of Arizona   (United States)

^b UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO CALCULATIONS; ADIABATIC ELECTRON AFFINITY; BOND DISSOCIATION ENERGIES; COUPLED-CLUSTER THEORY; PHOTOELECTRON IMAGING; SINGLET-TRIPLET SPLITTING; SUBSTITUTION EFFECT; VERTICAL DETACHMENT ENERGIES;

BOND STRENGTH (CHEMICAL); PHOTOELECTRON SPECTROSCOPY; PHOTOELECTRONS; PHOTONS;

ORGANIC COMPOUNDS;

EID: 84886882818     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp4053117     Document Type: Article

References (49)

1. Blanksby, S. J.; Ellison, G. B. Bond Dissociation Energies of Organic Molecules Acc. Chem. Res. 2003, 36, 255-263
2. 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
3. Tomioka, H. Persistent Triplet Carbenes Acc. Chem. Res. 1997, 30, 315-321
4. Rauk, A. Orbital Interaction Theory of Organic Chemistry; John Wiley & Sons Inc.: New York, NY, 1994.
5. -: Photoelectron Angular Distributions and Neutral Triplet Excitation Energies J. Phys. Chem. 1992, 96, 1130-1141
6. -) with Carbonyl Compounds Faraday Trans. I 1976, 72, 1601-1608
7. Lee, J.; Grabowski, J. J. Reactions of the Atomic Oxygen Radical-Anion and the Synthesis of Organic Reactive Intermediates Chem. Rev. 1992, 92, 1611-1647
8. Sanov, A.; Mabbs, R. Photoelectron Imaging of Negative Ions Int. Rev. Phys. Chem. 2008, 27, 53-85
9. Mabbs, R.; Grumbling, E. R.; Pichugin, K.; Sanov, A. Photoelectron Imaging: An Experimental Window into Electronic Structure Chem. Soc. Rev. 2009, 38, 2169-2177
10. Vogelhuber, K. M.; Wren, S. W.; McCoy, A. B.; Ervin, K. M.; Lineberger, W. C. Photoelectron Spectra of Dihalomethyl Anions: Testing the Limits of Normal Mode Analysis J. Chem. Phys. 2011, 134, 184306
11. -: The Convergence of Theory and Experiment after a Decade of Debate Phys. Chem. Chem. Phys. 2009, 11, 4745-4753
12. Thomas, P. S.; Bowling, N. P.; McMahon, R. J. Spectroscopy and Photochemistry of Triplet Methylpentadiynylidene J. Am. Chem. Soc. 2009, 131, 8649-8659
13. Bowling, N. P.; Halter, R. J.; Hodges, J. A.; Seburg, R. A.; Thomas, P. S.; Simmons, C. S.; Stanton, J. F.; McMahon, R. J. Reactive Carbon-Chain Molecules: Synthesis of 1-Diazo-2,4-Pentadiyne and Spectroscopic Characterization of Triplet Pentadiynylidene J. Am. Chem. Soc. 2006, 128, 3291-3302
14. - Reveals the Quasilinear Triplet Carbenes, HCCN and HCNC J. Chem. Phys. 2002, 117, 4323-4339
15. -: The Triplet Ground State and the Singlet-Triplet Splitting of Dicyanocarbene J. Chem. Phys. 2010, 132, 224301
16. - Cluster Anions J. Chem. Phys. 2006, 125, 114303
17. Wiley, W. C.; McLaren, I. H. Time-of-Flight Mass Spectrometer with Improved Resolution Rev. Sci. Instrum. 1955, 26, 1150
18. Eppink, A. T. J. B.; Parker, D. H. Velocity Map Imaging of Ions and Electrons Using Electrostatic Lenses: Application in Photoelectron and Photofragment Ion Imaging of Molecular Oxygen Rev. Sci. Instrum. 1997, 68, 3477-3484
19. Chandler, D. W.; Houston, P. L. Two-Dimensional Imaging of State-Selected Photodissociation Products Detected by Multiphoton Ionization J. Chem. Phys. 1987, 87, 1445-1447
20. Dribinski, V.; Ossadtchi, A.; Mandelshtam, V. A.; Reisler, H. Reconstruction of Abel-Transformable Images: The Gaussian Basis-Set Expansion Abel Transform Method Rev. Sci. Instrum. 2002, 73, 2634-2642
21. Heck, A. J. R.; Chandler, D. W. Imaging Techniques for the Study of Chemical-Reaction Dynamics Annu. Rev. Phys. Chem. 1995, 46, 335-372
22. Neumark, D. M.; Lykke, K. R.; Andersen, T.; Lineberger, W. C. Laser Photodetachment Measurement of the Electron-Affinity of Atomic Oxygen Phys. Rev. A 1985, 32, 1890-1892
23. - Photode-tachment Fine-Structure Transitions Phys. Rev. A 2007, 76, 052708
24. - J. Phys. Chem. 1994, 98, 8295-8301
25. Grumbling, E. R.; Pichugin, K.; Velarde, L.; Sanov, A. Further Evidence for Resonant Photoelectron-Solvent Scattering in Nitrous Oxide Cluster Anions J. Phys. Chem. A 2010, 114, 1367-1373
26. 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.1 ed.; Gaussian, Inc.: Wallingford, CT, 2009.
27. Krylov, A. I. Spin-Flip Configuration Interaction: An Electronic Structure Model that is Both Variational and Size-Consistent Chem. Phys. Lett. 2001, 338, 522-530
28. Levchenko, S. V.; Krylov, A. I. Equation-of-Motion Spin-Flip Couple-Cluster Model with Single and Double Substitutions: Theory and Application to Cyclobutadiene J. Chem. Phys. 2004, 120, 175-185
29. Slipchenko, L. V.; Krylov, A. I. Spin-Conserving and Spin-Flipping Equation-of-Motion Couple-Cluster Method with Triple Excitations J. Chem. Phys. 2005, 123, 084107
30. Krylov, A. I. Equation-of-Motion Coupled-Cluster Methods for Open-Shell and Electronically Excited Species: The Hitchhiker's Guide to Fock Space Annu. Rev. Phys. Chem. 2008, 59, 433-462
31. Manohar, P. U.; Krylov, A. I. A Noniterative Perturbative Triples Correction for the Spin-Flipping and Spin-Conserving Equation-of-Motion Coupled-Cluster Methods with Single and Double Substitutions J. Chem. Phys. 2008, 129, 194105
32. Shao, Y.; Molnar, L. F.; Jung, Y.; Kussmann, J.; Ochsenfeld, C.; Brown, S. T.; Gilbert, A. T. B.; Slipchenko, L. V.; Levchenko, S. V.; O'Neill, D. P. Advances in Methods and Algorithms in a Modern Quantum Chemistry Program Package Phys. Chem. Chem. Phys. 2006, 8, 3172-3191
33. Wigner, E. P. On the Behavior of Cross Sections near Thresholds Phys. Rev. 1948, 73, 1002-1009
34. Mead, R. D.; Lykke, K. R.; Lineberger, W. C. Photodetachment Threshold Laws. In Electronic and Atomic Collisions; Eichler, J.; Hertel, I. V.; Stolterfoht, N., Eds.; Elsevier: Amsterdam, 1984; pp 721-730.
35. -: Excited-State Dynamics of the Covalent Dimer Anion Phys. Rev. Lett. 2003, 90, 093001
36. Surber, E.; Sanov, A. Photoelectron Imaging of Carbonyl Sulfide Cluster Anions: Isomer Coexistence and Competition of Excited-State Decay Mechanisms J. Chem. Phys. 2003, 118, 9192-9200
37. Feller, D.; Peterson, K. A. Probing the Limits of Accuracy in Electronic Structure Calcula-tions: Is Theory Capable of Results Uniformly Better Than "Chemical Accuracy"? J. Chem. Phys. 2007, 126, 114105
38. - + Acetaldehyde Reaction Products: Search for Singlet Formylmethylene, a Wolff Rearrangement Intermediate J. Phys. Chem. A 2011, 115, 3208-3217
39. Bartmess, J. E. Negative Ion Energetics Data. In NIST Chemistry Webbook, NIST Standard Reference Database Number 69; Linstrom, P. J.; Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg MD, 20899, http://webbook.nist.gov (retrieved May 7, 2013), 2009.
40. Poutsma, J. C.; Upshaw, S. D.; Squires, R. R.; Wenthold, P. G. Absolute Heat of Formation and Singlet-Triplet Splitting for Hccn J. Phys. Chem. A 2002, 106, 1067-1073
41. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003.
42. - J. Am. Chem. Soc. 1987, 109, 5996-6003
43. Goebbert, D. J.; Velarde, L.; Khuseynov, D.; Sanov, A. C-H Bond Dissociation Energies of Acetonitrile and Malononitrile J. Phys. Chem. Lett. 2010, 1, 792-795
44. Viehe, H. G.; Janousek, Z.; Merenyi, R.; Stella, L. The Captodative Effect Acc. Chem. Res. 1985, 18, 148-154
45. Sanov, A.; Grumbling, E. R.; Goebbert, D. J.; Culberson, L. M. Photodetachment Anisotropy for Mixed S-P Orbitals: 8/3 and Other Fractions J. Chem. Phys. 2013, 138, 054311
46. Slipchenko, L. V.; Krylov, A. I. Singlet-Triplet Gaps in Diradicals by the Spin-Flip Approach: A Benchmark Study J. Chem. Phys. 2002, 117, 4694-4708
47. - J. Chem. Phys. 1985, 83, 4849-4865
48. Gronert, S.; Keeffe, J. R.; O'Ferrall, R. A. M. Stabilities of Carbenes: Independent Measures for Singlets and Triplets J. Am. Chem. Soc. 2011, 133, 3381-3389
49. Wagman, D. D.; Evans, W. H.; Parker, V. B.; Schumm, R. H.; Halow, I.; Bailey, S. M.; Churney, K. L.; Nuttall, R. L. The NBS Tables of Chemical Thermodynamic Properties (NBS Tech Note 270) J. Phys. Chem. Ref. Data, Suppl. 1 1982, 11