Theoretical study on the anomeric effect in carbene compound xc:ch2f (x = ch3, nh2, oh)
文献类型：期刊论文
| 作者 | Liu, Tao2,3; Yuan, Fang4; Li, Bing-Chao2; Yu, Zhang-Yu1 |
| 刊名 | Journal of molecular structure-theochem
 |
| 出版日期 | 2010-07-15 |
| 卷号 | 951期号:1-3页码:82-88 |
| 关键词 | Anomeric effect Xc:ch2f Xoch2f Mp2 Nbo |
| ISSN号 | 0166-1280 |
| DOI | 10.1016/j.theochem.2010.04.012 |
| 通讯作者 | Yu, zhang-yu(zhy_yu@126.com) |
| 英文摘要 | Ab initio calculations up to mp2/aug-cc-pvtz level have been carried out to study the anomeric effect in carbene compound xc:ch2f (x = ch3, nh2, oh, respectively) of singlet state and triplet state. for comparison, we also investigate the anomeric effect in xoch2f (x = ch3, nh2, oh, respectively) of singlet state and triplet state. the calculations indicate that the gauche conformers are more stable in every case than that of the corresponding anti conformers. we suggest that the five-membered intramolecular c(n,o)-h center dot center dot center dot f hydrogen bonds play an important role in stabilizing the gauche conformation of these compounds. the negative hyperconjugation between the carbene lone pair and the anti-bonding c-2-f orbital (ip(c:) -> sigma*(c-2-f)) results in stabilization of the antiperiplanar orientation of the c-2-f bond relative to the carbene lone pair. in the singlet state of xc:ch2f, sigma*(c-2-f) is well correlated with c-1-c-2 and c-2-f bond length due to anomeric effect. (c) 2010 elsevier b.v. all rights reserved. |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Physical |
| 语种 | 英语 |
| WOS记录号 | WOS:000278905000013 |
| 出版者 | ELSEVIER SCIENCE BV |
| URI标识 | http://www.irgrid.ac.cn/handle/1471x/2407684 |
| 专题 | 中国科学院大学 |
| 通讯作者 | Yu, Zhang-Yu |
| 作者单位 | 1.Shandong Univ, Sch Chem & Chem Engn, Jinan 250010, Shandong, Peoples R China 2.Jining Univ, Dept Chem & Chem Engn, Qufu 273155, Shandong, Peoples R China 3.Chinese Acad Sci, Grad Sch, Coll Chem & Chem Engn, Beijing 100049, Peoples R China 4.Qufu Normal Univ, Sch Math Sci, Qufu 273165, Shandong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Tao,Yuan, Fang,Li, Bing-Chao,et al. Theoretical study on the anomeric effect in carbene compound xc:ch2f (x = ch3, nh2, oh)[J]. Journal of molecular structure-theochem,2010,951(1-3):82-88. |
| APA | Liu, Tao,Yuan, Fang,Li, Bing-Chao,&Yu, Zhang-Yu.(2010).Theoretical study on the anomeric effect in carbene compound xc:ch2f (x = ch3, nh2, oh).Journal of molecular structure-theochem,951(1-3),82-88. |
| MLA | Liu, Tao,et al."Theoretical study on the anomeric effect in carbene compound xc:ch2f (x = ch3, nh2, oh)".Journal of molecular structure-theochem 951.1-3(2010):82-88. |
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来源：中国科学院大学
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