Aromaticity of closed-shell charged polybenzenoid hydrocarbons

Journal of Physical Chemistry A

Volumn 117, Issue 22, 2013, Pages 4679-4687

  Ramos Berdullas, Nicolás ^a   Radenković, Slavko ^b   Bultinck, Patrick ^c   Mandado, Marcos ^a  

^a UNIVERSITY OF VIGO   (Spain)

^b UNIVERSITY OF KRAGUJEVAC   (Serbia)

^c GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; GRAPH THEORY; POSITIVE IONS; SHELLS (STRUCTURES); STABILIZATION;

AROMATIC STABILIZATION; COMBUSTION CONDITION; DELOCALIZATION INDEXES; ELECTRON DELOCALIZATION; ELECTRONIC DELOCALIZATION; HYDROCARBON FRAGMENTS; INTERSTELLAR MEDIUMS; TOPOLOGICAL RESONANCE ENERGY;

AROMATIC HYDROCARBONS;

EID: 84879468446     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp401629k     Document Type: Article

References (58)

1. Dreyer, D. R.; Ruoff, R. S.; Bielawski, C. W. From Conception to Realization: An Historial Account of Graphene and Some Perspectives for Its Future Angew. Chem., Int. Ed. 2010, 49, 9336-9344
2. Geim, A. K. Random Walk to Graphene (Nobel Lecture) Angew. Chem., Int. Ed. 2011, 50, 6966-6985
3. Geim, A. K.; Novoselov, K. S. The Rise of Graphene Nat. Mater. 2007, 6, 183-191
4. Geim, A. K. Graphene: Status and Prospects Science 2009, 324, 1530-1534
5. Schmitz-Hübsch, T.; Sellam, F.; Staub, R.; Törker, M.; Fritz, T.; Kübel, Ch.; Müllen, K.; Leo, K. Direct Observation of Organic-Organic Heteroepitaxy: Perylene-tetracarboxylic-dianhydride on Hexa-peri-benzocoronene on Highly Ordered Pyrolytic Graphite Surf. Sci. 2000, 445, 358-367
6. Dötz, F.; Brand, J. D.; Ito, S.; Gherghel, L.; Müllen, K. Synthesis of Large Polycyclic Aromatic Hydrocarbons: Variation of Size and Periphery J. Am. Chem. Soc. 2000, 122, 7707-7717
7. Simpson, C. D.; Brand, J. D.; Berresheim, A. J.; Przybilla, L.; Räder, H. J.; Müllen, K. Synthesis of a Giant 222 Carbon Graphite Sheet Chem.-Eur. J. 2002, 8, 1424-1429
8. Stabel, A.; Herwig, P.; Müllen, K.; Rabe, P. Diodelike Current-Voltage Curves for a Single Molecule-Tunneling Spectroscopy with Submolecular Resolution of an Alkylated, peri-Condensed Hexabenzocoronene Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611
9. Müller, M.; Kübel, Ch.; Müllen, K. Giant Polycyclic Aromatic Hydrocarbons Chem.-Eur. J. 1998, 4, 2099-2109
10. Berresheim, A. J.; Müller, M.; Müllen, K. Polyphenylene Nanostructures Chem. Rev. 1999, 99, 1747-1786
11. Joachim, C.; Kazimierz, J.; Gimzewski, K. A Nanoscale Single-Molecule Amplifier and Its Consequences Proc. IEEE 1998, 86, 184-190
12. Bréchignac, P.; Pino, T. Electronic Spectra of Cold Gas Phase PAH Cations: Towards the Identification of the Diffuse Interstellar Bands Carriers Astron. Astrophys. 1999, 343, L49-L52
13. Gillett, F. C.; Forrest, W. J.; Merrill, K. M. 8-13-micron Spectra of NGC 7027, BD +30 3639, and NGC 6572 Astrophys. J. 1973, 183, 87-93
14. Tielens, A. G. G. M. Interstellar Polycyclic Aromatic Hydrocarbon Molecules Annu. Rev. Astron. Astrophys. 2008, 46, 289-337 and references therein
15. See for instance: Salama, F. PAHs in Astronomy-A Review. In Organic Matter in Space, Proceedings of the IAU Symposium; Kwok, S.; Sandford, S., Eds.; Cambridge University Press: Cambridge, U.K., 2008; pp 357 - 365 and references therein.
16. Hudgins, D. M.; Bauschlicher, C. W., Jr.; Allamandola, L. J. Closed-shell Polycyclic Aromatic Hydrocarbon Cations: A New Category of Interstellar Polycyclic Aromatic Hydrocarbons Spectrochim. Acta, Part A 2001, 57, 907-930
17. Rhee, Y. M.; Lee, T. J.; Gudipati, M. S.; Allamandola, L. J.; Head-Gordon, M. Charged Polycyclic Aromatic Hydrocarbon Clusters and the Galactic Extended Red Emission Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 5274-5278
18. Zhao, L.; Lian, R.; Shkrob, I. A.; Crowell, R. A.; Pommeret, S.; Chronister, E. L.; Liu, A. D.; Trifunac, A. D. Ultrafast Studies on the Photophysics of Matrix-Isolated Radical Cations of Polycyclic Aromatic Hydrocarbons J. Phys. Chem. A 2004, 108, 25-31
19. Witt, A. N.; Gordon, K. D.; Vijh, U. P.; Sell, P. H.; Smith, T. L.; Xie, R. H. The Excitation of Extended Red Emission: New Constraints on Its Carrier from Hubble Space Telescope Observations of NGC 7023 Astrophys. J. 2006, 636, 303-315
20. Weisman, J. L.; Lee, T. J.; Head-Gordon, M. Electronic Spectra and Ionization Potentials of a Stable Class of Closed Shell Polycyclic Aromatic Hydrocarbon Cations Spectrochim. Acta, Part A 2001, 57, 931-945
21. Troy, T. P.; Kable, S. H.; Schmidt, T. W.; Reid, S. A. On the Electronic Spectroscopy of Closed-shell Cations Derived from Resonance-stabilized Radicals: Insights from Theory and Franck-Condon Analysis Astron. Astrophys. 2012, 541, A8.1-A8.6
22. Weilmünster, P.; Keller, A.; Homann, K.-H. Large Molecules, Radicals, Ions, and Small Soot Particles in Fuel-rich Hydrocarbon Flames: Part I: Positive Ions of Polycyclic Aromatic Hydrocarbons(PAH) in Low-pressure Premixed Flames of Acetylene and Oxygen Combust. Flame 1998, 116, 62-83
23. Sethson, I.; Johnels, D.; Elflun, U.; Sygula, A. Based on H, Li, and C NMR Chemical Shifts of Phenalenyl Ions, It is Argued That the Observed Diamagnetism of the Systems is Due to the Diatropic Benzene and Naphthalene Subcircuits. MNDO and Graph Theoretical Calculations Support This Observation J. Chem. Soc., Perkin Trans. 2 1990, 1339-1341
24. Cyrański, M. K.; Havenith, R. W. A.; Dobrowolski, M. A.; Benjamin, R. G.; Krygowski, T. M.; Fowler, P. W.; Jenneskens, L. W. The Phenalenyl Motif: A Magnetic Chameleon Chem.-Eur. J. 2007, 13, 2201-2207
25. Randić, M. Relative Stability of Cations and Anions of Conjugated Polycyclic Hydrocarbons J. Phys. Chem. 1982, 86, 3970-3977
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; Gaussian, Inc.: Wallingford, CT, 2009.
27. Bultinck, P.; Ponec, R.; Van Damme, S. Multicenter Bond Indices as a New Measure of Aromaticity in Polycyclic Aromatic Hydrocarbons J. Phys. Org. Chem. 2005, 18, 706-718
28. Mandado, M.; González-Moa, M. J.; Mosquera, R. A. QTAIM n-Center Delocalization Indices as Descriptors of Aromaticity in Mono and Poly Heterocycles J. Comput. Chem. 2007, 28, 127-136
29. Mulliken, R. S. Electronic Population Analysis on LCAO (Single Bond) MO Molecular Wave Functions. I J. Chem. Phys. 1955, 23, 1833-1840
30. Mulliken, R. S. Electronic Population Analysis on LCAO (Single Bond) MO Molecular Wave Functions. II. Overlap Populations, Bond Orders, and Covalent Bond Energies J. Chem. Phys. 1955, 23, 1841-1846
31. Mulliken, R. S. Electronic Population Analysis on LCAO-MO Molecular Wave Functions. III. Effects of Hybridization on Overlap and Gross AO Populations J. Chem. Phys. 1955, 23, 2338-2342
32. Mulliken, R. S. Electronic Population Analysis on LCAO-MO Molecular Wave Functions. IV. Bonding and Antibonding in LCAO and Valence-Bond Theories J. Chem. Phys. 1955, 23, 2343-2346
33. Fowler, P. W.; Steiner, E. Pseudo-π Currents: Rapid and Accurate Visualisation of Ring Currents in Conjugated Hydrocarbons Chem. Phys. Lett. 2002, 364, 259-266
34. Monaco, G.; Viglione, R. G.; Zanasi, R.; Fowler, P. W. Designing Ring-Current Patterns: [10,5]-Coronene, a Circulene with Inverted Rim and Hub Currents J. Phys. Chem. A 2006, 110, 7447-7452
35. London, F. Théorie Quantique Des Courants Interatomiques Dans Les Combinaisons Aromatiques J. Phys. Radium 1937, 8, 397-409
36. Keith, T. A.; Bader, R. F. W. Calculation of Magnetic Response Properties Using a Continuous Set of Gauge Transformations Chem. Phys. Lett. 1993, 210, 223-231
37. Keith, T. A.; Bader, R. F. W. Topological Analysis of Magnetically Induced Molecular Current Distributions J. Chem. Phys. 1993, 99, 3669-3682
38. Coriani, S.; Lazzeretti, P.; Malagoli, M.; Zanasi, R. On CHF Calculations of Second-order Magnetic Properties Using the Method of Continuous Transformation of Origin of the Current Density Theor. Chim. Acta 1994, 89, 181-192
39. Steiner, E.; Fowler, P. W. Ring Currents in Aromatic Hydrocarbons Int. J. Quantum Chem. 1996, 60, 609-616
40. Bultinck, P.; Mandado, M.; Mosquera, R. A. The Pseudo-π Method Examined for the Computation of Multicenter Aromaticity Indices J. Math. Chem. 2008, 43, 111-118
41. Aihara, J. A New Definition of Dewar-type Resonance Energies J. Am. Chem. Soc. 1976, 98, 2750-2758
42. Gutman, I.; Milun, M.; Trinajstic, N. Graph Theory and Molecular Orbitals. 19. Nonparametric Resonance Energies of Arbitrary Conjugated Systems J. Am. Chem. Soc. 1977, 99, 1692-1704
43. Bosanac, S.; Gutman, I. Effect of a Ring on the Stability of Polycyclic Conjugated Molecules Z. Naturforsch., A: Phys. Sci. 1977, 32, 10-12
44. Gutman, I.; Bosanac, S. Quantitative Approach to Hückel Rule: The Relations Between the Cycles of a Molecular Graph and the Thermodynamic Stability of a Conjugated Molecule Tetrahedron 1977, 33, 1809-1812
45. Gutman, I. Cyclic Conjugation Energy Effects in Polycyclic π-electron Systems Monatsh. Chem. 2005, 136, 1055-1069
46. Radenković, S.; Gutman, I.; Bultinck, P. Comparative Study of Aromaticity in Tetraoxa[8]circulenes J. Phys. Chem. A 2012, 116, 9421-9430
47. Mandado, M.; González-Moa, M. J.; Mosquera, R. A. Chemical Graph Theory and n-center Electron Delocalization Indices: A Study on Polycyclic Aromatic Hydrocarbons J. Comput. Chem. 2007, 28, 1625-1633
48. Steiner, E.; Fowler, P.; Jenneskens, L. W. Counter-Rotating Ring Currents in Coronene and Corannulene Angew. Chem., Int. Ed. 2001, 40, 362-366
49. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Eikema Hommes, N. J. R. Nucleus-Independent Chemical Shifts: A Simple and Efficient Aromaticity Probe J. Am. Chem. Soc. 1996, 118, 6317-6318
50. Fias, S.; Fowler, P. W.; Delgado, J. L.; Hahn, U.; Bultinck, P. Correlation of Delocalization Indices and Current-Density Maps in Polycyclic Aromatic Hydrocarbons Chem.-Eur. J. 2008, 14, 3093-3099
51. Cyrański, M. K. Energetic Aspects of Cyclic Pi-Electron Delocalization: Evaluation of the Methods of Estimating Aromatic Stabilization Energies Chem. Rev. 2005, 105, 3773-3811
52. Ponec, R.; Fias, S.; Van Damme, S.; Bultinck, P.; Gutman, I.; Stanković, S. The Close Relation Between Cyclic Delocalization, Energy Effects of Cycles and Aromaticity Collect. Czech. Chem. Commun. 2009, 74, 147-166
53. Cioslowski, J.; Matito, E.; Solà, M. Properties of Aromaticity Indices Based on the One-electron Density Matrix J. Phys. Chem. A 2007, 111, 6521-6525
54. Mandado, M. Theoretical Basis for the Correlation Between Energetic, Magnetic, and Electron Density Criteria of Aromaticity: Definition of Molecular Circuit Electric Conductance Theor. Chem. Acc. 2010, 126, 339-349
55. Herndon, W. C.; Ellzey, M. L., Jr. Resonance Theory. V. Resonance Energies of Benzenoid and Nonbenzenoid π Systems J. Am. Chem. Soc. 1974, 96, 6631-6642
56. Mandado, M. Determination of London Susceptibilities and Ring Current Intensities Using Conjugated Circuits J. Chem. Theory Comput. 2009, 5, 2694-2701
57. Randić, M. Aromaticity of Polycyclic Conjugated Hydrocarbons Chem. Rev. 2003, 103, 3449-3606
58. Simpson, W. T. On the Use of Structures as an Aid in Understanding II-Electron Spectra- J. Am. Chem. Soc. 1953, 75, 597-603