Isolation and structural proof of the large diamond molecule, cyclohexamantane (C26H30)

Angewandte Chemie - International Edition

Volumn 42, Issue 18, 2003, Pages 2040-2044

  Dahl, Jeremy E P ^a,b   Moldowan, J Michael ^b   Peakman, Torren M ^c   Clardy, Jon C ^d   Lobkovsky, Emil ^d   Olmstead, Marilyn M ^e   May, Paul W ^f   Davis, Tim J ^f   Steeds, John W ^f   Peters, Ken E ^g   Pepper, Andy ^h   Ekuan, Andy ^b   Carlson, Robert M K ^a  

^a Catalyst Group   (United States)

^b STANFORD UNIVERSITY   (United States)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^d Department of Molecular Biology and Genetics   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

^f UNIVERSITY OF BRISTOL   (United Kingdom)

^g U S GEOLOGICAL SURVEY   (United States)

^h BP AMERICA INC   (United States)

Author keywords

Cage compounds; Carbon; Geochemistry; Hydrocarbons; Petroleum

Indexed keywords

CRUDE PETROLEUM; CRYSTAL STRUCTURE; HYDROCARBONS; X RAY CRYSTALLOGRAPHY;

CYCLOHEXAMANTANE;

SYNTHETIC DIAMONDS;

ADAMANTANE DERIVATIVE; CYCLOALKANE; CYCLOHEXAMANTANE; DIAMOND; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; ISOMERISM; MOLECULAR MODEL; RAMAN SPECTROMETRY; SCANNING ELECTRON MICROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037648568     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250794     Document Type: Article

References (27)

1. J. Ristein in Properties, Growth and Application of Diamond (Eds.: M. H. Nazare, A. J. Neves), Inspec, London, 2001, pp. 73-75.
2. G. Kopidakis, S. Aubry, Physica B 2001, 296, 237-250.
3. P. Badziag, W. S. Verwoerd, W. P. Ellis, N. R. Greiner, Nature 1990, 343, 244-245.
4. M. Shen, H. F. Schaefer, C. Liang, J-H. Lii, N. L. Allinger, P. von R. Schleyer, J. Am. Chem. Soc. 1992, 114, 497-505.
5. H. Hoft, Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives, Wiley-VCH, Weinheim, 2000, p. 547.
6. A. T. Balaban, P. von R Schleyer, Tetrahedron 1978, 34, 3599-3606.
7. J. E. Dahl, S. G. Liu, R. M. K. Carlson, Science 2003, 299, 96-99. Published online 28 November 2002.
8. P. von R. Schleyer in Cage Hydrocarbons (Ed: G. A. Olah), Wiley, New York, 1990, pp. 1-38.
9. M. A. McKervey, Tetrahedron 1980, 36, 971-992.
10. J. E. P. Dahl, J. M. Moldowan, K. E. Peters, G. E. Claypool, M. A. Rooney, G. E. Michael, M. R. Mello, M. L. Kohnen, Nature 1999, 399, 54-57.
11. S. Prawer, J. L. Peng, J. O. Orwa, J. C. McCallum, D. N. Jamieson, L. A. Bursill, Phys. Rev. B 2000, 360-363
12. F. H. Ree, N. W. Winter, J. N. Glosli, J. A. Viecelli, Physica B 1999, 265, 223-229.
13. P. Badziag, W. S. Verwoerd, W. P. Ellis, N. R. Greiner, Nature 1990, 343, 244-245.
14. H. W. Whitlock, M. W. Siefkien, J. Am. Chem. Soc. 1968, 90, 4929-4939.
15. T. M. Grund, P. von R. Schleyer, P. H. Gund, W. T. Wipke, J. Am. Chem. Soc. 1975 97, 743-751.
16. -1. Cyclohexamantane-containing distillation residue (0.10 mL) was injected neat and fractions were monitored by GC-MS. Cyclohexamantane spontaneously crystallized out of complex mixtures in HPLC fractions in the acetone mobile phase.
17. -3. CCDC-202094 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
18. L. Bistiricic, G. Baranovic, K.A. Mlinaric-Marjerkie, Spectrochim. Acta Part A 1995, 51, 1643-1664.
19. S. A. Solin, A. K. Ramdas, Phys. Rev. B 1970, 1687-1698.
20. S. Prawer, K. W. Nugent, D. N. Jamieson, J. O. Orwa, L. A. Bursill, J. L. Peng, Chem. Phys. Lett. 2000, 332, 93-97.
21. J. Pacansky, R. J. Waltman, J. Phys. Chem. 1995, 99, 3014-3019.
22. S. Prawer, K. W. Nugent, D. N. Jamieson, Diamond Relat. Mater. 1998, 7, 106-110.
23. M. L. Dheu, D. Gagnaire, H. Duddeck, F. Hollowood, M. A. McKervey, J. Chem. Soc. Perkin Trans. 2 1979, 357-359.
24. R. Lin, Z. Wilk, Fuel 1995, 74, 1512-1521.
25. H. Kamioka, K. Shibata, I. Kajizuka, T. Ohta, Geochem. J. 1996, 30, 189-194.
26. D. Shelkov, A. B. Verkhovskii, H. J. Milledge, C. T. Pillinger, Geol. Geofiz. 1997, 38, 315-322.
27. Y. L. Orlov, Mineralogy of the Diamond, Wiley, New York, 1972.