Direct and Catalytic Hydrogenation of Buckminsterfullerene C<sub>60</sub>

Sui, Yunlong; Jiuxin, Qian; Zhang, Jing; Zhou, Xuhao; Gu, Zhennan; Wu, Yi; Fu, Hua; Wang, Jingzun

doi:10.1080/10641229608001144

Cited by 8 publications

(3 citation statements)

References 9 publications

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“…The 500 MHz 1 H spectrum of the C 60 H 36 sample (band 2) prepared by DHA reduction is shown in Figure . This spectrum exhibits a level of spectral detail considerably greater than that previously reported at an unspecified field strength for a sample of C 60 H 36 that was prepared by catalytic hydrogenation of C 60 over Pd/C in toluene; however, the overall similarity of the spectra obtained by the two groups is obvious. While Sui and co-workers 45 did not propose any structures, the spectral similarity suggests that catalytic hydrogenation 45 and dihydroanthracene reduction yielded very similar products.…”

Section: Resultscontrasting

confidence: 50%

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C₆₀H₃₆

et al. 2001

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Isomers of C(60)H(36) and He@C(60)H(36) have been synthesized by the Birch or dihydroanthracene reduction of C(60) and isolated by preparative high-pressure liquid chromatography. (3)He, (13)C, and (1)H NMR spectroscopic properties were then determined. A comparison of experimental chemical shifts against those computed using density functional theory (B3LYP) with polarized triple- and double-zeta basis sets for He and C,H, respectively, allowed provisional assignment of structure for several isomers to be made. Theoretical calculations have also been carried out to identify low-energy structures. The transfer hydrogenation method using dihydroanthracene gives a major C(60)H(36) isomer and a minor C(60)H(36) isomer with C(3) symmetry as determined by the (13)C NMR spectrum of C(60)H(36) and the (3)He NMR spectrum of the corresponding sample of (3)He@C(60)H(36). In view of the HPLC retention times and the (3)He chemical shifts observed for the Birch and dihydroanthracene reduction products, the two isomers generated by the latter procedure can be only minor isomers of the Birch reduction. A significant energy barrier apparently exists in the dihydroanthracene reduction of C(60) for the conversion of the C(3) and C(1) symmetry isomers of C(60)H(36) to the T symmetry isomer previously predicted by many calculations to be among the most stable C(60)H(36) isomers. Many of the (1)H NMR signals exhibited by C(60)H(36) (and C(60)H(18), previously reported) are unusually deshielded compared to "ordinary" organic compounds, presumably because the unusual structures of C(60)H(36) and C(60)H(18) result in chemical shift tensors with one or more unusual principal values. Calculations clearly show a relationship between exceptionally deshielded protons beta to a benzene ring in C(60)H(18) and C(60)H(36) and relatively long C-C bonds associated with these protons. The additional information obtained from 1D and 2D (1)H NMR spectra obtained at ultrahigh field strengths (up to 900 MHz) will serve as a critical test of chemical shifts to be obtained from future calculations on different C(60)H(36) isomers.

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Section: Resultscontrasting

confidence: 50%

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C₆₀H₃₆

et al. 2001

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“…[75] However, the overall similarity of the spectra obtained by the two groups [74,75] is obvious. While Sui and co-workers [75] did not propose any structures, the spectral similarity suggests that catalytic hydrogenation [75] and dihydroanthracene reduction [74] yielded very similar products. The level of spectral detail shown in the 500-MHz spectrum [74] is far greater than that previously shown [5a,27a,29a, 76,77] or indicated [4,10,27b,78] in other samples of C 60 H 36 .…”

Section: (D) C 60 H 36 and C 60 H 18mentioning

confidence: 99%

The Synthesis and Characterization of Fullerene Hydrides

et al. 2001

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“…It is a stable, easily isolable species of limited solubility that persists for years. Numerous methods of synthesis have produced product slates that contain C 60 H 18 species including direct hydrogenation using 80 atm of H 2 (Sui et al 1996), hydrogenation in a hot filament chemical vapor modification (CVM) reactor using 20 torr of H 2 (Vieira et al 2001, and a transfer hydrogenation using 9,10-dihydroanthracene ). In the first and last of these cases, characterization of products was accomplished by mass spectrometry and little is known about their detailed structures.…”

Section: H 18mentioning

confidence: 99%

Fulleranes

2010

Carbon Materials: Chemistry and Physics

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A comprehensive book series which encompasses the complete coverage of carbon materials and carbon-rich molecules from elemental carbon dust in the interstellar medium, to the most specialized industrial applications of elemental carbon and its derivatives. A great emphasis is placed on the most advanced and promising applications ranging from electronics to medicinal chemistry. The aim is to offer the reader a book series which not only consists of self-sufficient reference works, but one which stimulates further research and enthusiasm. Series EditorsVolume 2: Fulleranes: The Hydrogenated Fullerenes Volume Editors

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Direct and Catalytic Hydrogenation of Buckminsterfullerene C₆₀

Cited by 8 publications

References 9 publications

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C₆₀H₃₆

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C₆₀H₃₆

The Synthesis and Characterization of Fullerene Hydrides

Fulleranes

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Direct and Catalytic Hydrogenation of Buckminsterfullerene C60

Cited by 8 publications

References 9 publications

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C60H36

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C60H36

The Synthesis and Characterization of Fullerene Hydrides

Fulleranes

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Product

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Direct and Catalytic Hydrogenation of Buckminsterfullerene C₆₀

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C₆₀H₃₆

Formation, Isolation, Spectroscopic Properties, and Calculated Properties of Some Isomers of C₆₀H₃₆