DOI: 10.1126/science.259.5103.1885. C 60 H 2 : Synthesis of the Simplest C 60 Hydrocarbon Derivative

C 60 H 2 : Synthesis of the Simplest C 60 Hydrocarbon Derivative

10.1126/science.259.5103.1885

Crossref journal-article

American Association for the Advancement of Science (AAAS)

Science (221)

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 (1a1b isomer). The 1 H nuclear magnetic resonance (NMR) spectrum of the product remained a sharp singlet between –80° and +100°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.

Bibliography

Henderson, C. C., & Cahill, P. A. (1993). C 60 H 2 â¯: Synthesis of the Simplest C 60 Hydrocarbon Derivative. Science, 259(5103), 1885â1887.

Authors 2

Craig C. Henderson (first)
Paul A. Cahill (additional)

References 13 Referenced 197

BIRKETT, P.R., PREPARATION AND CHARACTERIZATION OF C60BR6 AND C60BR8, NATURE 357: 479 (1992). (10.1038/357479a0) / NATURE (1992)
CREEGAN, K.M., SYNTHESIS AND CHARACTERIZATION OF (C60)O, THE 1ST FULLERENE EPOXIDE, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 114: 1103 (1992). (10.1021/ja00029a058) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1992)
ELEMES, Y, REACTION OF C-60 WITH DIMETHYLDIOXIRANE - FORMATION OF AN EPOXIDE AND A 1,3-DIOXOLANE DERIVATIVE, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH 31: 351 (1992). (10.1002/anie.199203511) / ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH (1992)
FAGAN, P.J., METAL-COMPLEXES OF BUCKMINSTERFULLERENE (C-60), ACCOUNTS OF CHEMICAL RESEARCH 25: 134 (1992). (10.1021/ar00015a006) / ACCOUNTS OF CHEMICAL RESEARCH (1992)
HAUFLER, R.E., EFFICIENT PRODUCTION OF C60 (BUCKMINSTERFULLERENE), C60H36, AND THE SOLVATED BUCKIDE ION, JOURNAL OF PHYSICAL CHEMISTRY 94: 8634 (1990). (10.1021/j100387a005) / JOURNAL OF PHYSICAL CHEMISTRY (1990)
HAWKINS, J.M., OSMYLATION OF C-60 - PROOF AND CHARACTERIZATION OF THE SOCCER-BALL FRAMEWORK, ACCOUNTS OF CHEMICAL RESEARCH 25: 150 (1992). (10.1021/ar00015a008) / ACCOUNTS OF CHEMICAL RESEARCH (1992)
HENDERSON, C.C., ANGEW CHEM INT EDIT 31: 1468 (1992). (10.1002/anie.199214681) / ANGEW CHEM INT EDIT (1992)
HENDERSON, C.C., SEMIEMPIRICAL CALCULATIONS OF THE ISOMERIC C60 DIHYDRIDES, CHEMICAL PHYSICS LETTERS 198: 570 (1992). (10.1016/0009-2614(92)85032-6) / CHEMICAL PHYSICS LETTERS (1992)
KOEFOD, R.S., ORGANOMETALLIC CHEMISTRY WITH BUCKMINSTERFULLERENE - PREPARATION AND PROPERTIES OF AN INDENYLIRIDIUM(I) COMPLEX, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 113: 8957 (1991). (10.1021/ja00023a060) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1991)
KRATSCHMER, W, SOLID C-60 - A NEW FORM OF CARBON, NATURE 347: 354 (1990). (10.1038/347354a0) / NATURE (1990)
MATSUZAWA, N, SEMIEMPIRICAL CALCULATIONS OF DIHYDROGENATED BUCKMINSTERFULLERENES, C60H2, JOURNAL OF PHYSICAL CHEMISTRY 96: 7594 (1992). (10.1021/j100198a021) / JOURNAL OF PHYSICAL CHEMISTRY (1992)
10.1126/science.254.5035.1186
10.1126/science.256.5058.822

Dates

Type	When
Created	18 years, 10 months ago (Oct. 5, 2006, 7:05 p.m.)
Deposited	1 year, 7 months ago (Jan. 12, 2024, 6:05 p.m.)
Indexed	11 months, 2 weeks ago (Sept. 7, 2024, 6:40 a.m.)
Issued	32 years, 4 months ago (March 26, 1993)
Published	32 years, 4 months ago (March 26, 1993)
Published Print	32 years, 4 months ago (March 26, 1993)

Funders 0

None

BibTeX

@article{Henderson_1993, title={C 60 H 2  : Synthesis of the Simplest C 60 Hydrocarbon Derivative}, volume={259}, ISSN={1095-9203}, url={http://dx.doi.org/10.1126/science.259.5103.1885}, DOI={10.1126/science.259.5103.1885}, number={5103}, journal={Science}, publisher={American Association for the Advancement of Science (AAAS)}, author={Henderson, Craig C. and Cahill, Paul A.}, year={1993}, month=mar, pages={1885–1887} }

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