Growth of fullerene fragments using the diels-alder cycloaddition reaction: First step towards a C60 synthesis by dimerization

Molecules

Volumn 18, Issue 2, 2013, Pages 2243-2254

  Mojica, Martha ^a   Méndez, Francisco ^a   Alonso, Julio A ^b  

^a DEPARTAMENTO DE QUÍMICA   (Mexico)

^b UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Diels Alder cycloaddition; Fullerene fragments; Pentacyclopentacorannulene; Transition states; Triindenetriphenilene

Indexed keywords

FULLERENE C60; FULLERENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; DIMERIZATION; ENTROPY; HYDROGENATION; KINETICS; METHODOLOGY;

CYCLOADDITION REACTION; DIMERIZATION; ENTROPY; FULLERENES; HYDROGENATION; KINETICS; MODELS, MOLECULAR;

MLCS; MLOWN;

EID: 84874598206     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18022243     Document Type: Article

References (36)

1. Kroto, H.W.; Heath, J.R.; O'Brien, S.C.; Curl, R.F.; Smalley, R.E. C60: Bukminsterfullerene. Nature 1985, 318, 162-163.
2. Krätschmer, W.; Fostiropoulos, K.; Huffman, D.R. The infrared and ultraviolet absorption spectra of laboratory-produced carbon dust: Evidence of the presence of the C60 molecule. Chem. Phys. Lett. 1990, 170, 167-170.
3. Scott, L.T.; Boorum, M.M.; McMahon, B.J.; Hagen, S.; Mack, J.; Blank, J.; Wegner, H.; de Meijere, A. A rational synthesis of C60. Science 2002, 295, 1500-1503.
4. Scott, L.T.; Petrukhina, M.A. Preface. In Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions and Coordination Chemistry; Scott, L.T., Petrukhina, M.A., Eds.; John Wiley & Sons: Hoboken, NJ, USA, 2012; pp. vii-x.
5. Krätschmer, W.; Lamb, L.D.; Fostiropoulos, K.; Huffman, D.R. Solid C60: A new form of carbon. Nature 1990, 347, 354-358.
6. Otero, G.; Biddau, G.; Sánchez-Sánchez, C.; Caillard, R.; López, M.F.; Rogero, C.; Palomares, F.J.; Cabello, N.; Basanta, M.A.; Ortega, J.; et al. Fullerenes from aromatic precursors by surface-catalysed cyclodehydrogenation. Nature 2008, 454, 865-868.
7. Scott, L.T. Methods for the chemical synthesis of fullerenes. Angew. Chem. Int. Ed. 2004, 43, 4994-5007. (Pubitemid 39330762)
8. Tsefrikas, V.M.; Scott, L.T. Geodesic polyarenes by flash vacuum pyrolysis. Chem. Rev. 2006, 106, 4868-4884. (Pubitemid 46099384)
9. Geneste, F.; Moradpour, A.; Dive, G.; Peeters, D.; Malthête, J.; Sadoc, J.-F. Retrosynthetic analysis of fullerene C60: Structure, stereochemistry, and calculated stability of C30 fragments. J. Org. Chem. 2002, 67, 605-607. (Pubitemid 34101271)
10. Abdourazak, A.H.; Marcinow, Z.; Sygula, A.; Sygula, R.; Rabideau, P.W. Buckybowls 2. Toward the total synthesis of Bukminsterfullerene (C60): Benz[5,6]-as-indaceno-[3,2,1,8,7- mnopqr]indeno[4,3,2,1-cdef]chrysene. J. Am. Chem. Soc. 1995, 117, 6410-6411.
11. Hagen, S.; Bratcher, M.S.; Erickson, M.S.; Zimmermann, G.; Scott, L.T. Novel syntheses of three C30H12 bowl-shaped polycyclic aromatic hydrocarbons. Angew. Chem. Int. Ed. 1997, 36, 406-408.
12. Anet, F.A.L.; Muira, S.S.; Siegel, J.; Mislow, K. La Coupe du Roi and its relevance to stereochemistry. Combination of two homochiral molecules to give an achiral product. J. Am. Chem. Soc. 1983, 105, 1419-1926.
13. Scott, L.T. Polycyclic aromatic hydrocarbon bowls, baskets, balls and tubes: Challenging targets for chemical synthesis. Polycyclic Aromat. Compd. 2010, 30, 247-259.
14. Fort, E.H.; Donovan, P.M.; Scott, L.T. Diels-Alder reactivity of polycyclic aromatic hydrocarbon bay regions: Implications for metal-free growth of single-chirality carbon nanotubes. J. Am. Chem. Soc. 2009, 131, 16006-16007.
15. Fort, E.H.; Scott, L.T. Gas-phase Diels-Alder cycloaddition of benzyne to an aromatic hydrocarbon bay region: Groundwork for the selective solvent-free growth of armchair carbon nanotubes. Tetrahedron Lett. 2011, 52, 2051-2053.
16. Fukui, K.; Yonezawa, T.; Shingu, H. A molecular-orbital theory of reactivity in aromatic hydrocarbons. J. Chem. Phys. 1952, 20, 722-725.
17. Fukui, K.; Yonezawa, T.; Nagata, C.; Shingu, H. Molecular-orbital theory of orientation in aromatic, heteroaromatic, and other conjugated molecules. J. Chem. Phys. 1954, 22, 1433-1442.
18. Flemig, I. Molecular Orbitals and Organic Chemical Reactions; John Wiley & Sons Ltd: London, UK, 2009; pp. 224-242.
19. Park, Y.S.; Lee, B.-S.; Lee, I. Density functional theory studies of hetero-Diels-Alder reactions. New J. Chem. 1999, 27, 707-715. (Pubitemid 29378831)
20. Hehre, W.J.; Radom, L.; Schleyer, P.v.R.; Pople, J.A. Ab Initio Molecular Orbital Theory; Wiley: New York, NY, USA, 1986; Chapter 4.
21. Mendoza, J.A.; García-Pérez, E.; Jiménez- Vázquez, H.A.; Tamariz, J. Effect of aryl substituents on the reactivity of the captodative olefins 1-acetylvinyl arenecarboxylates. J. Mex. Chem. Soc. 2006, 50, 47-56.
22. Houk, K.N.; Lin, Y.-T.; Brown, F.K. Evidence for the concerted mechanism of the Diels-Alder reaction of butadiene with ethylene. J. Am. Chem. Soc. 1986, 108, 554-556.
23. Houk, K.N.; Loncharich, R.J.; Blake, J.F.; Jorgensen, W.L. Substituent effects and transition structures for Diels-Alder reactions of butadiene and cyclopentadiene with cyanoalkenes. J. Am. Chem. Soc. 1989, 111, 9172-9176. (Pubitemid 20066161)
24. Guner, V.; Khuong, K.S.; Leach, A.G.; Lee, P.S.; Bartberger, M.D.; Houk, K.N. A standard set of pericyclic reactions of hydrocarbons for the benchmarking of computational methods: The performance of ab initio, Density functional, CASSCF, CASPT2, and CBS-QB3 methods for the prediction of activation barriers, Reaction energetics, and transition state geometries. J. Phys. Chem. A 2003, 107, 11445-11459.
25. Ishida, K.; Morokuma, K.; Komornic, A. The intrinsic reaction coordinate. An ab inito calculation for HNC-HCN and H-+CH4-CH4+H-. J. Chem. Phys. 1977, 66, 2153-2156.
26. Fukui, K. The paths of chemical reaction - The IRC approach. Acc. Chem. Res. 1981, 14, 363-368.
27. Gonzalez, C.; Schlegel, H.B. An improved algorithm for reaction path following. J. Chem. Phys. 1989, 90, 2154-2161.
28. Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E. Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene. J. Am. Chem. Soc. 1936, 58, 146-153.
29. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A., Jr.; Stratmann, R.E.; Burant, J.C.; et al. GAUSSIAN 03 (Revision A.9); Gaussian, Inc.: Pittsburgh, PA, USA, 2003.
30. Lee, K.H.; Lee, C.; Kang, J.; Park, S.S.; Lee, J.; Lee, S.K.; Bohme, D.K. Preferential site of attack on fullerene cations: Frontier orbitals and rate coefficients. J. Phys. Chem. A 2006, 110, 11730-11733. (Pubitemid 44806917)
31. Martinez, J.I.; Moncada, J.L.; Larenas, J.M. The dual descriptor to measure local reactivity on Buckminster fullerenes: An analysis within the framework of conceptual DFT. J. Mol. Model. 2010, 16, 1825-1832.
32. Petrukhina, M.A.; Andreini, K.W.; Mack, J.; Scott, L.T. X-ray quality geometries of geodesic polyarenes from theoretical calculations: What levels of theory are reliable? J. Org. Chem. 2005, 70, 5713-5716. (Pubitemid 40980783)
33. Osuna, S.; Morera, J.; Cases, M.; Morokuma, K.; Solà, M. Diels-Alder reaction between ciclopentadiene and C60: An analysis of the performance of the ONIOM method for the study of chemical reactivity in fullerenes and nanotubes. J. Phys. Chem. A 2009, 113, 9721-9726.
34. Ikuma, N.; Susami, Y.; Oshima, T. Kinetics and regioselectivity in the Diels-Alder reaction of fulleroids vs. methanofullerene and C60. Org. Biomol. Chem. 2010, 8, 1394-1398.
35. Suárez-Moreno, G.V.; González-Zamora, E.; Méndez, F. Oxazole as an electron-deficient diene in the Diels-Alder reaction. Org. Lett. 2011, 13, 6358-6361.
36. Damoun, S.; Van de Woude, G.; Méndez, F.; Geerlings, P. Local softness as a regioselectivity indicator in [4+2] cycloaddition reactions. J. Phys. Chem. A 1997, 101, 886-893. (Pubitemid 127578286)