Carbon rings decorated with group 14 elements: New aromatic clusters containing planar tetracoordinate carbon

Osvaldo Yañez, Alejandro Vásquez-Espinal, Rodrigo Báez-Grez, Walter A. Rabanal-León, Edison Osorio, Lina Ruiz, William Tiznado

Resultado de la investigación: Article

2 Citas (Scopus)

Resumen

A simple and chemically intuitive approach is used to design ptC-containing E-C clusters (E = Si-Pb). This approach consists in replacing three or two consecutive protons from an aromatic hydrocarbon by one E 2 4+ or one E 2+ fragment, respectively. In the model, electrons from E are removed from the p z orbitals, emptying them. Si-Pb favors the formation of a 3c-2e (E-C-E) σ-bond, which involves the ptC. Additionally, the π-electronic cloud is delocalized through the E-p z orbitals allowing the E atoms to effectively take part in the electronic delocalization, preserving the 4n + 2 Hückel's rule from the parent hydrocarbon. Two aromatic monocycles and one aromatic bicycle-benzene (C 6 H 6 ), cyclopentadienyl anion (C 5 H 5 - ) and pentalene dianion (C 8 H 6 2- )-have been transformed into C-E systems. After an extensive exploration of their potential energy surfaces, four new global minima with ptC are identified, resulting from the substitution of the protons by Si and Ge cations in C 5 H 5 - and C 8 H 6 2- (E 3 C 5 and E 4 C 8 ). The analysis of both the chemical bonding and the magnetic response to an external magnetic field confirms the aromatic character of these species.

Idioma originalEnglish
Páginas (desde-hasta)6781-6785
Número de páginas5
PublicaciónNew Journal of Chemistry
Volumen43
N.º17
DOI
EstadoPublished - 1 ene 2019

Huella dactilar

Chemical elements
Protons
Carbon
Aromatic Hydrocarbons
Potential energy surfaces
Bicycles
Aromatic hydrocarbons
Hydrocarbons
Benzene
Anions
Cations
Substitution reactions
Negative ions
Positive ions
Magnetic fields
Atoms
Electrons

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

Citar esto

Yañez, O., Vásquez-Espinal, A., Báez-Grez, R., Rabanal-León, W. A., Osorio, E., Ruiz, L., & Tiznado, W. (2019). Carbon rings decorated with group 14 elements: New aromatic clusters containing planar tetracoordinate carbon. New Journal of Chemistry, 43(17), 6781-6785. https://doi.org/10.1039/c9nj01022j
Yañez, Osvaldo ; Vásquez-Espinal, Alejandro ; Báez-Grez, Rodrigo ; Rabanal-León, Walter A. ; Osorio, Edison ; Ruiz, Lina ; Tiznado, William. / Carbon rings decorated with group 14 elements : New aromatic clusters containing planar tetracoordinate carbon. En: New Journal of Chemistry. 2019 ; Vol. 43, N.º 17. pp. 6781-6785.
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abstract = "A simple and chemically intuitive approach is used to design ptC-containing E-C clusters (E = Si-Pb). This approach consists in replacing three or two consecutive protons from an aromatic hydrocarbon by one E 2 4+ or one E 2+ fragment, respectively. In the model, electrons from E are removed from the p z orbitals, emptying them. Si-Pb favors the formation of a 3c-2e (E-C-E) σ-bond, which involves the ptC. Additionally, the π-electronic cloud is delocalized through the E-p z orbitals allowing the E atoms to effectively take part in the electronic delocalization, preserving the 4n + 2 H{\"u}ckel's rule from the parent hydrocarbon. Two aromatic monocycles and one aromatic bicycle-benzene (C 6 H 6 ), cyclopentadienyl anion (C 5 H 5 - ) and pentalene dianion (C 8 H 6 2- )-have been transformed into C-E systems. After an extensive exploration of their potential energy surfaces, four new global minima with ptC are identified, resulting from the substitution of the protons by Si and Ge cations in C 5 H 5 - and C 8 H 6 2- (E 3 C 5 and E 4 C 8 ). The analysis of both the chemical bonding and the magnetic response to an external magnetic field confirms the aromatic character of these species.",
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Yañez, O, Vásquez-Espinal, A, Báez-Grez, R, Rabanal-León, WA, Osorio, E, Ruiz, L & Tiznado, W 2019, 'Carbon rings decorated with group 14 elements: New aromatic clusters containing planar tetracoordinate carbon', New Journal of Chemistry, vol. 43, n.º 17, pp. 6781-6785. https://doi.org/10.1039/c9nj01022j

Carbon rings decorated with group 14 elements : New aromatic clusters containing planar tetracoordinate carbon. / Yañez, Osvaldo; Vásquez-Espinal, Alejandro; Báez-Grez, Rodrigo; Rabanal-León, Walter A.; Osorio, Edison; Ruiz, Lina; Tiznado, William.

En: New Journal of Chemistry, Vol. 43, N.º 17, 01.01.2019, p. 6781-6785.

Resultado de la investigación: Article

TY - JOUR

T1 - Carbon rings decorated with group 14 elements

T2 - New aromatic clusters containing planar tetracoordinate carbon

AU - Yañez, Osvaldo

AU - Vásquez-Espinal, Alejandro

AU - Báez-Grez, Rodrigo

AU - Rabanal-León, Walter A.

AU - Osorio, Edison

AU - Ruiz, Lina

AU - Tiznado, William

PY - 2019/1/1

Y1 - 2019/1/1

N2 - A simple and chemically intuitive approach is used to design ptC-containing E-C clusters (E = Si-Pb). This approach consists in replacing three or two consecutive protons from an aromatic hydrocarbon by one E 2 4+ or one E 2+ fragment, respectively. In the model, electrons from E are removed from the p z orbitals, emptying them. Si-Pb favors the formation of a 3c-2e (E-C-E) σ-bond, which involves the ptC. Additionally, the π-electronic cloud is delocalized through the E-p z orbitals allowing the E atoms to effectively take part in the electronic delocalization, preserving the 4n + 2 Hückel's rule from the parent hydrocarbon. Two aromatic monocycles and one aromatic bicycle-benzene (C 6 H 6 ), cyclopentadienyl anion (C 5 H 5 - ) and pentalene dianion (C 8 H 6 2- )-have been transformed into C-E systems. After an extensive exploration of their potential energy surfaces, four new global minima with ptC are identified, resulting from the substitution of the protons by Si and Ge cations in C 5 H 5 - and C 8 H 6 2- (E 3 C 5 and E 4 C 8 ). The analysis of both the chemical bonding and the magnetic response to an external magnetic field confirms the aromatic character of these species.

AB - A simple and chemically intuitive approach is used to design ptC-containing E-C clusters (E = Si-Pb). This approach consists in replacing three or two consecutive protons from an aromatic hydrocarbon by one E 2 4+ or one E 2+ fragment, respectively. In the model, electrons from E are removed from the p z orbitals, emptying them. Si-Pb favors the formation of a 3c-2e (E-C-E) σ-bond, which involves the ptC. Additionally, the π-electronic cloud is delocalized through the E-p z orbitals allowing the E atoms to effectively take part in the electronic delocalization, preserving the 4n + 2 Hückel's rule from the parent hydrocarbon. Two aromatic monocycles and one aromatic bicycle-benzene (C 6 H 6 ), cyclopentadienyl anion (C 5 H 5 - ) and pentalene dianion (C 8 H 6 2- )-have been transformed into C-E systems. After an extensive exploration of their potential energy surfaces, four new global minima with ptC are identified, resulting from the substitution of the protons by Si and Ge cations in C 5 H 5 - and C 8 H 6 2- (E 3 C 5 and E 4 C 8 ). The analysis of both the chemical bonding and the magnetic response to an external magnetic field confirms the aromatic character of these species.

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U2 - 10.1039/c9nj01022j

DO - 10.1039/c9nj01022j

M3 - Article

AN - SCOPUS:85065180501

VL - 43

SP - 6781

EP - 6785

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

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Yañez O, Vásquez-Espinal A, Báez-Grez R, Rabanal-León WA, Osorio E, Ruiz L y otros. Carbon rings decorated with group 14 elements: New aromatic clusters containing planar tetracoordinate carbon. New Journal of Chemistry. 2019 ene 1;43(17):6781-6785. https://doi.org/10.1039/c9nj01022j