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    Conjugation-promoted reaction of open-cage fullerene: A density functional theory study

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    Type
    Article
    Authors
    Guo, Yong
    Yan, Jingjing
    Khashab, Niveen M. cc
    KAUST Department
    Numerical Porous Media SRI Center (NumPor)
    Smart Hybrid Materials (SHMs) lab
    Physical Sciences and Engineering (PSE) Division
    Chemical Science Program
    Advanced Membranes and Porous Materials Research Center
    Date
    2012-01-20
    Permanent link to this record
    http://hdl.handle.net/10754/562062
    
    Metadata
    Show full item record
    Abstract
    Density functional theory calculations are performed to study the addition mechanism of e-rich moieties such as triethyl phosphite to a carbonyl group on the rim of a fullerene orifice. Three possible reaction channels have been investigated. The obtained results show that the reaction of a carbonyl group on a fullerene orifice with triethyl phosphite most likely proceeds along the classical Abramov reaction; however, the classical product is not stable and is converted into the experimental product. An attack on a fullerene carbonyl carbon will trigger a rearrangement of the phosphate group to the carbonyl oxygen as the conversion transition state is stabilized by fullerene conjugation. This work provides a new insight on the reactivity of open-cage fullerenes, which may prove helpful in designing new switchable fullerene systems. Not that classical: The reaction of a carbonyl group on the fullerene orifice with triethyl phosphite most likely proceeds following the Abramov reaction to firstly form a classical product. However, this product is not stable and turns into an experimental product as the conversion transition state is stabilized by fullerene conjugation (see picture). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Sponsors
    We are grateful to King Abdullah University of Science and Technology (KAUST) for financial support.
    Publisher
    Wiley-Blackwell
    Journal
    ChemPhysChem
    ISSN
    14394235
    DOI
    10.1002/cphc.201100745
    PubMed ID
    22266747
    ae974a485f413a2113503eed53cd6c53
    10.1002/cphc.201100745
    Scopus Count
    Collections
    Articles; Controlled Release and Delivery Laboratory; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Advanced Membranes and Porous Materials Research Center

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