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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
HUANG HUI; STEWART TIMOTHY; GUTMANN MATTHIAS; OHHARA TAKASHI; NIIMURA NOBUO; Li YX(李玉学); WEN JIANFENG; BAU ROBERT; Huang NZ(黄乃正)
2009
发表期刊J. Org. Chem.
ISSN0022-3263
卷号74期号:1页码:359-369
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.
学科领域有机化学
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
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收录类别SCI
语种英语
WOS记录号WOS:000262004000042
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文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/27777
专题上海有机化学研究所
通讯作者BAU ROBERT; Huang NZ(黄乃正)
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GB/T 7714
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.
APA HUANG HUI.,STEWART TIMOTHY.,GUTMANN MATTHIAS.,OHHARA TAKASHI.,NIIMURA NOBUO.,...&黄乃正.(2009).To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene.J. Org. Chem.,74(1),359-369.
MLA HUANG HUI,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. Org. Chem. 74.1(2009):359-369.
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