Internal rotation in the singly bonded dimers of substituted C60. A molecular lever

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 257-265

  Ösawa, Shuichi ^a,b   Ösawa, Eiji ^a   Harada, Masaomi ^a,c  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c NITTO DENKO CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013544863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9511861     Document Type: Article

References (72)

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47. 8 adduct at room temperature: Roth, G.; Adelman, P. J. Phys. I Fr. 1992, 2, 1541.
48. 8 adduct at room temperature: Roth, G.; Adelman, P. J. Phys. I Fr. 1992, 2, 1541.
49. 8 adduct at room temperature: Roth, G.; Adelman, P. J. Phys. I Fr. 1992, 2, 1541.
50. 60. Bonds connecting two five-membercd rings (β and δ 1.39 Å) are distinctly shorter than those on the five-membered ring (α, γ, and ε, 1.45 Å). Bond η (1.41 Å) is unique for 2 in that it is exocyclic to only one pentagonal ring, hence significantly longer than β and δ, while θ, another new bond type is the longest of all (1.46 Å). For a new interpretation based on the bond alternation patterns, see ref 17.
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54. This assumption is reasonable when R substituents are large, because the equilibrium is shifted to the homogeneous dimer. However, mixed dimers may be significantly populated for dimers carrying small Rs.
55. Numerical details are deposited in supporting information.
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62. Note that the scale of abscissa is different in (a) and (b)
63. (a) Ösawa, S.; Ösawa, E. In Science and Technology of Fullerene Materials, Vol. 359, MRS Symposium Proceedings Series; Materials Research Society: Pittsburg, 1995; pp 145-156.
64. (b) Ösawa, S.; Ösawa, E. Fullerene Sci. Technol., in press.
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66. 60 bonds are rotated in separate two-bond drive runs while keeping the trans pivot conformation, this point became a sharp hilltop. The torsional energy surface is shown in Figure 6 of the supporting information.
67. The total steric energy curves correspond to the front end of the torsional energy surfaces shown in Figure 2. Namely, both tert-butyl groups are in a staggered conformation.
68. Examples are known on the stabilization of an apparently congested situation by van der Waals attraction: (a) Ösawa, E. In Advances in Molecular Structure Research, Vol. 2; Hargittai, I., Hargittai, M., Eds.; JAP Press: Connecticut, in press. (b) Tsuzuki, S.; Schafer, L.; Goto, H.; Jemmis, E. D.; Hosoya, H.; Tanabe, K.; Ösawa, E. J. Am. Chem. Soc. 1991, 113, 4665. (c) Cao, M.; Schäfer, L. J. Mol. Struct. (Theochem) 1993, 284, 235.
69. Examples are known on the stabilization of an apparently congested situation by van der Waals attraction: (a) Ösawa, E. In Advances in Molecular Structure Research, Vol. 2; Hargittai, I., Hargittai, M., Eds.; JAP Press: Connecticut, in press. (b) Tsuzuki, S.; Schafer, L.; Goto, H.; Jemmis, E. D.; Hosoya, H.; Tanabe, K.; Ösawa, E. J. Am. Chem. Soc. 1991, 113, 4665. (c) Cao, M.; Schäfer, L. J. Mol. Struct. (Theochem) 1993, 284, 235.
70. Examples are known on the stabilization of an apparently congested situation by van der Waals attraction: (a) Ösawa, E. In Advances in Molecular Structure Research, Vol. 2; Hargittai, I., Hargittai, M., Eds.; JAP Press: Connecticut, in press. (b) Tsuzuki, S.; Schafer, L.; Goto, H.; Jemmis, E. D.; Hosoya, H.; Tanabe, K.; Ösawa, E. J. Am. Chem. Soc. 1991, 113, 4665. (c) Cao, M.; Schäfer, L. J. Mol. Struct. (Theochem) 1993, 284, 235.
71. 60 cage.
72. 3, as we have found here.