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Predicting efficient C(60) epoxidation and viable multiple oxide formation by theoretical study

Manoharan1

  • 1Algemene Chemie(ALGC), Eenheid Faculteit Wetenschappen, Vrije Universiteit Brussel, Pleinlaan 2, B-1050, Brussels, Belgium.

The Journal of Organic Chemistry
|May 18, 2000
PubMed
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Computational studies reveal that strong electrophilic oxidizing agents significantly enhance fullerene epoxidation. Methyl(trifluoromethyl)dioxirane (MTMD) and bis(trifluoromethyl)dioxirane (BTMD) are identified as optimal for quantitative C(60)O production.

Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Fullerene epoxidation is a key reaction for functionalizing C(60).
  • Understanding the mechanism of epoxidation by dioxiranes is crucial for controlling reactivity.

Purpose of the Study:

  • To computationally investigate the epoxidation of C(60) using dimethyldioxirane (DMD), methyl(trifluoromethyl)dioxirane (MTMD), and bis(trifluoromethyl)dioxirane (BTMD).
  • To elucidate the reaction mechanisms and identify factors influencing the efficiency and selectivity of fullerene epoxidation.

Main Methods:

  • Computational probing using the AM1 method.
  • Analysis of frontier molecular orbitals (HOMO/LUMO) and electronic interactions.
  • Investigation of transition state geometries and reaction pathways.

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Main Results:

  • Dimethyldioxirane (DMD) reacts with C(60) via an inverse electron demand pathway involving HOMO-LUMO interactions.
  • Trifluoromethyl groups in MTMD and BTMD lower the oxidant's LUMO, enhancing nucleophilic attack on fullerene and increasing reaction rates.
  • MTMD and BTMD facilitate quantitative C(60)O production, while DMD can lead to multiple epoxidations (C(60)O(2), C(60)O(3)).
  • Regiochemistry of multiple oxidations favors adjacent sites due to increased nucleophilicity of epoxide-attached double bonds.

Conclusions:

  • Strong electrophilic oxidizing agents, particularly MTMD and BTMD, significantly enhance fullerene epoxidation efficiency.
  • The electronic effects of trifluoromethyl groups are key to achieving high yields of C(60)O.
  • Computational insights guide the selection of optimal reagents for selective fullerene functionalization.