Advanced search
1 file | 1.68 MB

Aromaticity of closed-shell charged polybenzenoid hydrocarbons

(2013) JOURNAL OF PHYSICAL CHEMISTRY A. 117(22). p.4679-4687
Author
Organization
Abstract
Abstract: The aromatic stabilization of closed-shell charged polybenzenoid hydrocarbons (PBHs) has been scrutinized by means of energetic and magnetic aromaticity criteria and by direct measures of electron delocalization. Thus, topological resonance energies and their circuit contributions, ring current maps, and multicenter delocalization indices have been calculated for a series of 18 polybenzenoid cations containing from 3 to 10 benzene rings. All calculations indicate that the closed-shell cations have a similar degree of aromaticity compared to that of the corresponding closed-shell neutral PBHs. All cations investigated display a large degree of electronic delocalization in the ring, accompanied by significant aromatic stabilization and a strong diatropic peripheral electron current. Graph theoretical models describe perfectly the aromatic features of these hydrocarbon fragments, showing how they can be understood as a superposition of specific neutral PBHs. The large aromatic character of these systems suggests they may be relatively stable upon formation at combustion conditions, like those given in the interstellar medium. It has been postulated that closed-shell fragments of PBHs may play an important role in the photoluminescent phenomenon known as extended red emission.
Keywords
EXTENDED RED EMISSION, DELOCALIZATION INDEXES, MOLECULAR WAVE FUNCTIONS, ELECTRONIC POPULATION ANALYSIS, RESONANCE ENERGIES, RING CURRENTS, CONJUGATED HYDROCARBONS, CURRENT-DENSITY, GRAPH-THEORY, CATIONS

Downloads

  • (...).pdf
    • full text
    • |
    • UGent only
    • |
    • PDF
    • |
    • 1.68 MB

Citation

Please use this url to cite or link to this publication:

Chicago
Ramos-Berdullas, Nicolás, Slavko Radenkovic, Patrick Bultinck, and Marcos Mandado. 2013. “Aromaticity of Closed-shell Charged Polybenzenoid Hydrocarbons.” Journal of Physical Chemistry A 117 (22): 4679–4687.
APA
Ramos-Berdullas, N., Radenkovic, S., Bultinck, P., & Mandado, M. (2013). Aromaticity of closed-shell charged polybenzenoid hydrocarbons. JOURNAL OF PHYSICAL CHEMISTRY A, 117(22), 4679–4687.
Vancouver
1.
Ramos-Berdullas N, Radenkovic S, Bultinck P, Mandado M. Aromaticity of closed-shell charged polybenzenoid hydrocarbons. JOURNAL OF PHYSICAL CHEMISTRY A. 2013;117(22):4679–87.
MLA
Ramos-Berdullas, Nicolás, Slavko Radenkovic, Patrick Bultinck, et al. “Aromaticity of Closed-shell Charged Polybenzenoid Hydrocarbons.” JOURNAL OF PHYSICAL CHEMISTRY A 117.22 (2013): 4679–4687. Print.
@article{4108571,
  abstract     = {Abstract: The aromatic stabilization of closed-shell charged polybenzenoid hydrocarbons (PBHs) has been scrutinized by means of energetic and magnetic aromaticity criteria and by direct measures of electron delocalization. Thus, topological resonance energies and their circuit contributions, ring current maps, and multicenter delocalization indices have been calculated for a series of 18 polybenzenoid cations containing from 3 to 10 benzene rings. All calculations indicate that the closed-shell cations have a similar degree of aromaticity compared to that of the corresponding closed-shell neutral PBHs. All cations investigated display a large degree of electronic delocalization in the ring, accompanied by significant aromatic stabilization and a strong diatropic peripheral electron current. Graph theoretical models describe perfectly the aromatic features of these hydrocarbon fragments, showing how they can be understood as a superposition of specific neutral PBHs. The large aromatic character of these systems suggests they may be relatively stable upon formation at combustion conditions, like those given in the interstellar medium. It has been postulated that closed-shell fragments of PBHs may play an important role in the photoluminescent phenomenon known as extended red emission.},
  author       = {Ramos-Berdullas, Nicol{\'a}s and Radenkovic, Slavko and Bultinck, Patrick and Mandado, Marcos},
  issn         = {1089-5639},
  journal      = {JOURNAL OF PHYSICAL CHEMISTRY A},
  keyword      = {EXTENDED RED EMISSION,DELOCALIZATION INDEXES,MOLECULAR WAVE FUNCTIONS,ELECTRONIC POPULATION ANALYSIS,RESONANCE ENERGIES,RING CURRENTS,CONJUGATED HYDROCARBONS,CURRENT-DENSITY,GRAPH-THEORY,CATIONS},
  language     = {eng},
  number       = {22},
  pages        = {4679--4687},
  title        = {Aromaticity of closed-shell charged polybenzenoid hydrocarbons},
  url          = {http://dx.doi.org/10.1021/jp401629k},
  volume       = {117},
  year         = {2013},
}

Altmetric
View in Altmetric
Web of Science
Times cited: