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学科主题: 有机化学
题名: To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene
其他题名: To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene
作者: HUANG HUI ; STEWART TIMOTHY ; GUTMANN MATTHIAS ; OHHARA TAKASHI ; NIIMURA NOBUO ; Li YX(李玉学) ; WEN JIANFENG ; BAU ROBERT ; Huang NZ(黄乃正)
通讯作者: BAU ROBERT ; 黄乃正
刊名: J. Org. Chem.
发表日期: 2009
卷: 74, 期:1, 页:359-369
收录类别: SCI
部门归属: Univ So Calif; Rutherford Appleton Lab; Japan Atom Energy Agcy; Ibaraki Univ; 上海有机所; 香港中文大学
英文摘要: Two chiral tetraphenylenes, 2,15-dideuteriotetraphenylene (7) and 2,7-dimethyltetraphenylene (15) were synthesized and resolved to address the tetraphenylene inversion barrier problem. Neutron diffraction investigation of enantiopure 7 showed that the molecule retained its chirality integrity during its synthesis from enantiopure precursors and therefore rules out the possibility of the tetraphenylene framework possessing a low-energy barrier to inversion. Thermal study on 15 and tetraphenylene I further revealed that their inversion barriers were not overcome up to 600 degrees C, at which temperature these compounds underwent skeletal contraction into triphenylene with activation energies of 62.8 and 58.2 kcal/mol, respectively. This result is supported by computational studies which yielded an inversion barrier of 135 kcal/mol for tetraphenylene as a consequence of the peri-hydrogen repulsions at its planar conformation.
语种: 英语
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WOS记录号: WOS:000262004000042
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/27777
Appears in Collections:上海有机化学研究所_期刊论文

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Recommended Citation:
HUANG HUI,STEWART TIMOTHY,GUTMANN MATTHIAS,et al. To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene[J]. J. Org. Chem.,2009,74(1):359-369.
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