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

Research output: Contribution to journalArticle

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5463-5470
Number of pages8
JournalJournal of Organic Chemistry
Volume79
Issue number12
DOIs
Publication statusPublished - 20 Jun 2014

ASJC Scopus subject areas

  • Organic Chemistry

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    Azpiroz, J. M., Islas, R., Moreno, D., Fernández-Herrera, M. A., Pan, S., Chattaraj, P. K., Martínez-Guajardo, G., Ugalde, J. M., & Merino, G. (2014). Carbo-cages: A computational study. Journal of Organic Chemistry, 79(12), 5463-5470. https://doi.org/10.1021/jo500488c