Lowering Inversion Barriers of Buckybowls by Benzannelation of the Rim: Synthesis and Crystal and Molecular Structure of 1,2-Dihydrocyclopenta[b,c]dibenzo[g,m]corannulene
作者： Zbigniew Marcinow , Andrzej Sygula , Arkady Ellern , Peter W. Rabideau
DOI: 10.1021/OL016607H
关键词: Inversion (discrete mathematics) 、 Chemistry 、 Molecule 、 Computational chemistry 、 Crystallography 、 Toluene 、 Proton NMR 、 Corannulene 、 Crystal structure 、 Yield (chemistry) 、 Crystal
摘要: [structure: see text]. The title compound (3) has been synthesized by a non-pyrolytic route providing 36% isolated yield in the final step. X-ray crystal structure determination shows that 3 crystallizes with one solvating molecule of toluene and exhibits slightly lower curvature than parent cyclopentacorannulene. DFT calculations predict substantially bowl-to-bowl inversion barrier for dihydro-cyclopentacorannulene, this is confirmed dynamic 1H NMR experiments.
acs.org
sci-hub.se 参考文章(19)
T. Jon Seiders, Kim K. Baldridge, Jay S. Siegel, Synthesis and Characterization of the First Corannulene Cyclophane Journal of the American Chemical Society. ,vol. 118, pp. 2754- 2755 ,(1996) , 10.1021/JA953734Y
T. Jon Seiders, Eric L. Elliott, Gunther H. Grube, Jay S. Siegel, Synthesis of Corannulene and Alkyl Derivatives of Corannulene Journal of the American Chemical Society. ,vol. 121, pp. 7804- 7813 ,(1999) , 10.1021/JA991310O
Lawrence T. Scott, Mohammed M. Hashemi, Matthew S. Bratcher, Corannulene bowl-to-bowl inversion is rapid at room temperature Journal of the American Chemical Society. ,vol. 114, pp. 1920- 1921 ,(1992) , 10.1021/JA00031A079
J. C. Hanson, C. E. Nordman, The crystal and molecular structure of corannulene, C20H10 Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. ,vol. 32, pp. 1147- 1153 ,(1976) , 10.1107/S0567740876012430
Andrzej Sygula, Haskell E. Folsom, Renata Sygula, Atteye H. Abdourazak, Zbigniew Marcinow, Frank R. Fronczek, Peter W. Rabideau, Bowl stacking in curved polynuclear aromatic hydrocarbons: crystal and molecular structure of cyclopentacorannulene Journal of The Chemical Society, Chemical Communications. pp. 2571- 2572 ,(1994) , 10.1039/C39940002571
Barry M. Trost, Pyracylenes. VII. Antiaromatic peripheral systems. Synthesis and chemistry of pyracyloquinone Journal of the American Chemical Society. ,vol. 91, pp. 918- 923 ,(1969) , 10.1021/JA01032A021
Eric L. Elliott, Gunther H. Grube, Jay S. Siegel, T. Jon Seiders, Kim K. Baldridge, Synthesis and Quantum Mechanical Structure of sym-Pentamethylcorannulene and Decamethylcorannulene Journal of the American Chemical Society. ,vol. 121, pp. 7439- 7440 ,(1999) , 10.1021/JA991486Q
Andrzej Sygula, Peter W. Rabideau, The First Non-Pyrolytic Synthesis of a Semibuckminsterfullerene Journal of the American Chemical Society. ,vol. 120, pp. 12666- 12667 ,(1998) , 10.1021/JA9828760
Peter W. Rabideau, Andrzej Sygula, Buckybowls: Polynuclear Aromatic Hydrocarbons Related to the Buckminsterfullerene Surface Accounts of Chemical Research. ,vol. 29, pp. 235- 242 ,(1996) , 10.1021/AR950197D
Andrzej Sygula, Atteye H. Abdourazak, Peter W. Rabideau, CYCLOPENTACORANNULENE : PI -FACIAL STEREOSELECTIVE DEUTEROGENATION AND DETERMINATION OF THE BOWL-TO-BOWL INVERSION BARRIER FOR A CONSTRAINED BUCKYBOWL Journal of the American Chemical Society. ,vol. 118, pp. 339- 343 ,(1996) , 10.1021/JA9521987