Carbo-cages: A computational study

Jon M. Azpiroz, Rafael Islas, Diego Moreno, María A. Fernández-Herrera, Sudip Pan, Pratim K. Chattaraj, Gerardo Martínez-Guajardo, Jesus M. Ugalde, Gabriel Merino

Resultado de la investigación: Article

11 Citas (Scopus)

Resumen

Inspired by their geometrical perfection, intrinsic beauty, and particular properties of polyhedranes, a series of carbo-cages is proposed in silico via density functional theory computations. The insertion of alkynyl units into the C-C bonds of polyhedranes results in a drastic lowering of the structural strain. The induced magnetic field shows a significant delocalization around the three-membered rings. For larger rings, the response is paratropic or close to zero, suggesting a nonaromatic behavior. In the carbo-counterparts, the values of the magnetic response are shifted with respect to their parent compounds, but the aromatic/nonaromatic character remains unaltered. Finally, Born-Oppenheimer molecular dynamics simulations at 900 K do not show any drastic structural changes up to 10 ps. In the particular case of a carbo-prismane, no structural change is perceived until 2400 K. Therefore, although carbo-cages have enthalpies of formation 1 order of magnitude higher than those of their parent compounds, their future preparation and isolation should not be discarded, because the systems are kinetically stable, explaining why the similar systems like carbo-cubane have already been synthesized.

Idioma originalEnglish
Páginas (desde-hasta)5463-5470
Número de páginas8
PublicaciónJournal of Organic Chemistry
Volumen79
N.º12
DOI
EstadoPublished - 20 jun 2014

Huella dactilar

Charcoal
Density functional theory
Molecular dynamics
Enthalpy
Magnetic fields
Computer simulation

ASJC Scopus subject areas

  • Organic Chemistry

Citar esto

Azpiroz, J. M., Islas, R., Moreno, D., Fernández-Herrera, M. A., Pan, S., Chattaraj, P. K., ... Merino, G. (2014). Carbo-cages: A computational study. Journal of Organic Chemistry, 79(12), 5463-5470. https://doi.org/10.1021/jo500488c
Azpiroz, Jon M. ; Islas, Rafael ; Moreno, Diego ; Fernández-Herrera, María A. ; Pan, Sudip ; Chattaraj, Pratim K. ; Martínez-Guajardo, Gerardo ; Ugalde, Jesus M. ; Merino, Gabriel. / Carbo-cages : A computational study. En: Journal of Organic Chemistry. 2014 ; Vol. 79, N.º 12. pp. 5463-5470.
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abstract = "Inspired by their geometrical perfection, intrinsic beauty, and particular properties of polyhedranes, a series of carbo-cages is proposed in silico via density functional theory computations. The insertion of alkynyl units into the C-C bonds of polyhedranes results in a drastic lowering of the structural strain. The induced magnetic field shows a significant delocalization around the three-membered rings. For larger rings, the response is paratropic or close to zero, suggesting a nonaromatic behavior. In the carbo-counterparts, the values of the magnetic response are shifted with respect to their parent compounds, but the aromatic/nonaromatic character remains unaltered. Finally, Born-Oppenheimer molecular dynamics simulations at 900 K do not show any drastic structural changes up to 10 ps. In the particular case of a carbo-prismane, no structural change is perceived until 2400 K. Therefore, although carbo-cages have enthalpies of formation 1 order of magnitude higher than those of their parent compounds, their future preparation and isolation should not be discarded, because the systems are kinetically stable, explaining why the similar systems like carbo-cubane have already been synthesized.",
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Azpiroz, JM, Islas, R, Moreno, D, Fernández-Herrera, MA, Pan, S, Chattaraj, PK, Martínez-Guajardo, G, Ugalde, JM & Merino, G 2014, 'Carbo-cages: A computational study', Journal of Organic Chemistry, vol. 79, n.º 12, pp. 5463-5470. https://doi.org/10.1021/jo500488c

Carbo-cages : A computational study. / Azpiroz, Jon M.; Islas, Rafael; Moreno, Diego; Fernández-Herrera, María A.; Pan, Sudip; Chattaraj, Pratim K.; Martínez-Guajardo, Gerardo; Ugalde, Jesus M.; Merino, Gabriel.

En: Journal of Organic Chemistry, Vol. 79, N.º 12, 20.06.2014, p. 5463-5470.

Resultado de la investigación: Article

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T1 - Carbo-cages

T2 - A computational study

AU - Azpiroz, Jon M.

AU - Islas, Rafael

AU - Moreno, Diego

AU - Fernández-Herrera, María A.

AU - Pan, Sudip

AU - Chattaraj, Pratim K.

AU - Martínez-Guajardo, Gerardo

AU - Ugalde, Jesus M.

AU - Merino, Gabriel

PY - 2014/6/20

Y1 - 2014/6/20

N2 - Inspired by their geometrical perfection, intrinsic beauty, and particular properties of polyhedranes, a series of carbo-cages is proposed in silico via density functional theory computations. The insertion of alkynyl units into the C-C bonds of polyhedranes results in a drastic lowering of the structural strain. The induced magnetic field shows a significant delocalization around the three-membered rings. For larger rings, the response is paratropic or close to zero, suggesting a nonaromatic behavior. In the carbo-counterparts, the values of the magnetic response are shifted with respect to their parent compounds, but the aromatic/nonaromatic character remains unaltered. Finally, Born-Oppenheimer molecular dynamics simulations at 900 K do not show any drastic structural changes up to 10 ps. In the particular case of a carbo-prismane, no structural change is perceived until 2400 K. Therefore, although carbo-cages have enthalpies of formation 1 order of magnitude higher than those of their parent compounds, their future preparation and isolation should not be discarded, because the systems are kinetically stable, explaining why the similar systems like carbo-cubane have already been synthesized.

AB - Inspired by their geometrical perfection, intrinsic beauty, and particular properties of polyhedranes, a series of carbo-cages is proposed in silico via density functional theory computations. The insertion of alkynyl units into the C-C bonds of polyhedranes results in a drastic lowering of the structural strain. The induced magnetic field shows a significant delocalization around the three-membered rings. For larger rings, the response is paratropic or close to zero, suggesting a nonaromatic behavior. In the carbo-counterparts, the values of the magnetic response are shifted with respect to their parent compounds, but the aromatic/nonaromatic character remains unaltered. Finally, Born-Oppenheimer molecular dynamics simulations at 900 K do not show any drastic structural changes up to 10 ps. In the particular case of a carbo-prismane, no structural change is perceived until 2400 K. Therefore, although carbo-cages have enthalpies of formation 1 order of magnitude higher than those of their parent compounds, their future preparation and isolation should not be discarded, because the systems are kinetically stable, explaining why the similar systems like carbo-cubane have already been synthesized.

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Azpiroz JM, Islas R, Moreno D, Fernández-Herrera MA, Pan S, Chattaraj PK y otros. Carbo-cages: A computational study. Journal of Organic Chemistry. 2014 jun 20;79(12):5463-5470. https://doi.org/10.1021/jo500488c