C[sub 60]H[sub 2]: Synthesis of the simplest C[sub 60] hydrocarbon derivative
- Sandia National Laboratories, Albuquerque, NM (United States)
The reaction of C[sub 60] with BH[sub 3]:tetrahydrofuran in toluene followed by hydrolysis yielded C[sub 60]H[sub 2]. This product was separated by high-performance liquid chromatography and characterized as the addition product of H[sub 2] to a 6,6-ring fusion (1a1b isomer). The [sup 1]H nuclear magnetic resonance (NMR) spectrum of the product remained a sharp singlet between [minus]80[degrees] and +100[degrees]C, which suggests a static structure on the NMR time scale. Hydrolysis of the proposed borane addition product with acetic acid-d[sub 1] or D[sub 2]O yielded C[sub 60]HD, and its [sup 3]J[sub HD] coupling constant is consistent with vicinal addition. The observation of a single C[sub 60]H[sub 2] isomer is in complete agreement with earlier calculations that indicated that at most 2 of the 23 possible isomers of C[sub 60] would be observable at equilibrium at room temperature. These results suggest that organoborane chemistry may be applied to further functionalization of fullerenes. 13 refs., 5 figs.
- DOE Contract Number:
- AC04-76DP00789
- OSTI ID:
- 6539148
- Journal Information:
- Science (Washington, D.C.); (United States), Journal Name: Science (Washington, D.C.); (United States) Vol. 259:5103; ISSN SCIEAS; ISSN 0036-8075
- Country of Publication:
- United States
- Language:
- English
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Process for fullerene functionalization
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACETIC ACID
ALKYLATED AROMATICS
AROMATICS
BORANES
BOROHYDRIDES
BORON COMPOUNDS
CARBON
CARBOXYLIC ACIDS
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHROMATOGRAPHY
ELEMENTS
EQUILIBRIUM
FULLERENES
FURANS
HEAVY WATER
HETEROCYCLIC COMPOUNDS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
ISOMERS
LIQUID COLUMN CHROMATOGRAPHY
MAGNETIC RESONANCE
MONOCARBOXYLIC ACIDS
NONMETALS
NUCLEAR MAGNETIC RESONANCE
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXYGEN COMPOUNDS
RESONANCE
SEPARATION PROCESSES
SYNTHESIS
TETRAHYDROFURAN
TOLUENE
WATER