To Flip or Not To Flip? Assessing the Inversion Barrier of the Tetraphenylene Framework with Enantiopure 2,15-Dideuteriotetraphenylene and 2,7-Dimethyltetraphenylene
文献类型：期刊论文
| 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) |
| 刊名 | J. Org. Chem.
 |
| 出版日期 | 2009 |
| 卷号 | 74期号:1页码:359-369 |
| ISSN号 | 0022-3263 |
| 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 |
| 通讯作者 | BAU ROBERT ; 黄乃正 |
| 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. |
| 学科主题 | 有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/jo802061p |
| 语种 | 英语 |
| WOS记录号 | WOS:000262004000042 |
| 公开日期 | 2013-08-21 |
| 源URL | [http://202.127.28.38/handle/331003/27777]  |
| 专题 | 上海有机化学研究所_上海有机化学研究所 |
| 推荐引用方式 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. |
入库方式： OAI收割
来源：上海有机化学研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。