ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Carbo-Cages: A Computational Study

View Author Information
Kimika Fakultatea, Euskal Herriko Unibertsitatea (UPV/EHU), and Donostia International Physics Center (DIPC), P. K. 1072, 20080 Donostia, Euskadi, Spain
Departamento de Física Aplicada, Centro de Investigación y de Estudios Avanzados, Unidad Mérida, Km 6 Antigua Carretera a Progreso. Apdo. Postal 73, Cordemex, 97310, Mérida, Yuc., México
§ Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 72570, Puebla, Pue., México
Department of Chemistry and Centre for Theoretical Studies, Indian Institute of Technology, Kharagpur, 721302, India
Unidad Académica de Ciencias Químicas, Área de Ciencias de la Salud, Universidad Autónoma de Zacatecas, Km. 6 carretera Zacatecas-Guadalajara s/n, Ejido La Escondida C. P. 98160, Zacatecas, Zac., Mexico
*E-mail: [email protected] (G.M.).
*E-mail: [email protected] (J.M.U.).
Cite this: J. Org. Chem. 2014, 79, 12, 5463–5470
Publication Date (Web):May 20, 2014
Copyright © 2014 American Chemical Society

    Article Views





    Other access options
    Supporting Info (2)»


    Abstract Image

    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.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    Jump To

    The geometries of the parent polyhedranes and enthalpies of formation and geometrical parameters of cubane and carbo-cubane computed using different functionals. Born–Oppenheimer molecular dynamics simulation movies at 900 K for carbo-1 to carbo-9 in mp4 format are provided in a compressed zip file. This material is available free of charge via the Internet at

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system:

    Cited By

    This article is cited by 13 publications.

    1. David Arias-Olivares, Andrés Becerra-Buitrago, Luis Carlos García-Sánchez, Diego V. Moreno, Rafael Islas. In Silico Analysis of the Aromaticity of Some Carbo-Metallabenzenes and Carbo-Dimetallabenzenes (Carbo-mers Proposed from Metallabenzenes). ACS Omega 2024, 9 (9) , 10913-10928.
    2. Atif Mahmood, Maria Dimitrova, Lukas N. Wirz, Dage Sundholm. Magnetically Induced Current Densities in π-Conjugated Porphyrin Nanoballs. The Journal of Physical Chemistry A 2022, 126 (43) , 7864-7873.
    3. Filipe Agapito, Rui C. Santos, Rui M. Borges dos Santos, and José A. Martinho Simões . The Thermochemistry of Cubane 50 Years after Its Synthesis: A High-Level Theoretical Study of Cubane and Its Derivatives. The Journal of Physical Chemistry A 2015, 119 (12) , 2998-3007.
    4. Camila M. B. Machado, Nathalia B. D. Lima, Sóstenes L. S. Lins, Alfredo M. Simas. A theorized new class of polyhedral hydrocarbons of molecular formula CnHn and their bottom-up scaffold expansions into hyperstructures. Scientific Reports 2021, 11 (1)
    5. Mesías Orozco-Ic, Albeiro Restrepo, Alvaro Muñoz-Castro, Gabriel Merino. Molecular Helmholtz coils. The Journal of Chemical Physics 2019, 151 (1)
    6. Cristian Tirapegui, Macarena Rojas-Poblete, Ramiro Arratia-Perez, Cristian Linares-Flores, Rafael Islas, Eduardo Schott, Raul Guajardo-Maturana. Optical and electronic properties of benzopyrylium derivatives. Theoretical-experimental synergy towards novel DSSCs devices. Dyes and Pigments 2019, 161 , 370-381.
    7. Rafael Islas, Diego P. Oyarzún, Plinio Cantero-López. Analysis of the aromaticity in extended systems formed from isoelectronic Al42− and C42+ aromatic clusters. Structural Chemistry 2018, 29 (5) , 1383-1395.
    8. Konstantin P. Katin, Mikhail M. Maslov. Thermal stability of carbon [ n ,5] prismanes ( n = 2–4): a molecular dynamics study. Molecular Simulation 2018, 44 (9) , 703-707.
    9. Yenni P. Ortiz, Douglas J. Klein, Joel F. Liebman. Paradigms and paradoxes. Tetrahedral units: dodecahedral super-structures. Structural Chemistry 2018, 29 (1) , 89-96.
    10. Alejandro Vásquez-Espinal, Jordi Poater, Miquel Solà, William Tiznado, Rafael Islas. Testing the effectiveness of the isoelectronic substitution principle through the transformation of aromatic osmathiophene derivatives into their inorganic analogues. New Journal of Chemistry 2017, 41 (3) , 1168-1178.
    11. Kévin Cocq, Christine Lepetit, Valérie Maraval, Remi Chauvin. “Carbo-aromaticity” and novel carbo-aromatic compounds. Chemical Society Reviews 2015, 44 (18) , 6535-6559.
    12. Fabio Pichierri. Hypercubane: DFT-based prediction of an O-symmetric double-shell hydrocarbon. Chemical Physics Letters 2014, 612 , 198-202.
    13. Said Jalife, Martha Audiffred, Rafael Islas, Sigfrido Escalante, Sudip Pan, Pratim K. Chattaraj, Gabriel Merino. The inorganic analogues of carbo -benzene. Chemical Physics Letters 2014, 610-611 , 209-212.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect