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C60H2: Synthesis of the Simplest C60 Hydrocarbon Derivative | | Craig C Henderson
; Paul A Cahill
; | | Date: |
26 Mar 1993 | | Journal: | Science, 259 (5103), 1885-1887 | | Abstract: | The reaction of C(60) with BH(3): tetrahydrofuran in toluene followed by hydrolysis yielded C(60)H(2). This product was separated by high-performance liquid chromatography and characterized as the addition product of H(2) to a 6,6-ring fusion (1alb isomer). The (1)H nuclear magnetic resonance (NMR) spectrum of the product remained a sharp singlet between -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(1) or D(2)O yielded C(60)HD, and its (3)J(HD) coupling constant is consistent with vicinal addition. The observation of a single C(60)H(2) isomer is in complete agreement with earlier calculations that indicated that at most 2 of the 23 possible isomers of C(60) would be observable at equilibrium at room temperature. These results suggest that organoborane chemistry may be applied to further functionalization of fullerenes. | | Source: | PubMed, pmid17836247 doi: 10.1126/science.259.5103.1885 | | Services: | Forum | Review | Favorites | |
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