Locking the bowl-shaped geometry of corannulene. Cyclopentacorannulene

Journal Article · Wed Apr 07 00:00:00 EDT 1993 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00060a073· OSTI ID:6300975

Abdourazak, A H; Sygula, A; Rabideau, P W ^[1]

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1. Louisiana State Univ., Baton Rouge (United States)

The discovery that buckminsterfullerene, C[sub 60], is a stable molecule due to geodesic and electronic properties inherent in the truncated icosahedral cage structure has generated a renewed interest in hydrocarbons with curved surfaces. The carbon framework of corannulene, which can be considered to represent the polar cap of buckminsterfullerene, is surprisingly flexible. In spite of its substantial curvature, corannulene undergoes rapid bowl-to-bowl inversion in solution, and this raises the question as to how many additional fused rings on the corannulene structure will be required to lock the bowl conformation. Herein we provide the answer that the bowl becomes rigid, at aleast on the NMR time scale, with only the addition of two carbons in a fused five-membered ring. 12 refs.

• OSTI ID: 6300975
• Journal Information: Journal of the American Chemical Society; (United States), Vol. 115:7; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AROMATICS
MOLECULAR STRUCTURE
FULLERENES
HYDROGENATION
NUCLEAR MAGNETIC RESONANCE
PYROLYSIS
SYNTHESIS
CARBON
CHEMICAL REACTIONS
DECOMPOSITION
ELEMENTS
MAGNETIC RESONANCE
NONMETALS
ORGANIC COMPOUNDS
RESONANCE
THERMOCHEMICAL PROCESSES
360600* - Other Materials
360602 - Other Materials- Structure & Phase Studies
400201 - Chemical & Physicochemical Properties