Hydrogen-bonding-mediated anthranilamide homoduplexes. Increasing stability through preorganization and iterative arrangement of a simple amide binding site
文献类型：期刊论文
| 作者 | Zhu J(朱江) ; Lin JB(林建斌) ; Xu YX(徐云祥) ; Shao XB(邵学斌) ; Jiang XK(蒋锡夔) ; Li ZT(黎占亭) |
| 刊名 | J. Am. Chem. Soc.
 |
| 出版日期 | 2006 |
| 卷号 | 128期号:37页码:12307-12313 |
| ISSN号 | 0002-7863 |
| 其他题名 | 氢键介质的芳酰胺同体二聚体: 通过预组织和简单酰胺结合位点的连续排列增强稳定性 |
| 通讯作者 | 黎占亭 |
| 英文摘要 | This paper describes the assembly of two new series of self-complementary duplexes by making use of amide units, the simplest assembling units of hydrogen bonding, as binding sites. All the new monomers possess a rigidified anthranilamide skeleton, which is stabilized by intramolecular hydrogen bonding. Amide units are iteratively introduced to one side of the preorganized skeletons to facilitate the formation of intermolecular hydrogen bonding. Compounds 2 and 3 bear two and three CONH2 units, respectively, while 4, 6, and 7 are incorporated with two, three, and four AcNH units, respectively. For comparison, compound 5, which is similar to 4 but contains one AcNH and one CF3CONH unit, is also prepared. X-ray diffraction analysis of 2, 4, and 5 revealed homodimeric motifs in the solid state which are stabilized by two or more intermolecular hydrogen bonds. H-1 NMR investigations in CDCl3 indicated that all the compounds form hydrogen-bonded homoduplexes. Duplexes 3(.)3, 6(.)6, and 7(.)7 are highly stable in CDCl3, with a lower K-assoc limit of 2.3 x 10(5) M-1. The K-assoc values of the three duplexes in more polar CDCl3/CD3CN (9:1, v/v) were determined with the H-1 NMR dilution method. The result opens the way for the development of new polymeric duplexes of well-ordered structures. |
| 学科主题 | 物理有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/ja064218i |
| 语种 | 英语 |
| WOS记录号 | WOS:000240465200053 |
| 公开日期 | 2013-01-16 |
| 源URL | [http://202.127.28.38/handle/331003/12690]  |
| 专题 | 上海有机化学研究所_物理有机化学研究室 |
| 推荐引用方式 GB/T 7714 | Zhu J,Lin JB,Xu YX,et al. Hydrogen-bonding-mediated anthranilamide homoduplexes. Increasing stability through preorganization and iterative arrangement of a simple amide binding site[J]. J. Am. Chem. Soc.,2006,128(37):12307-12313. |
| APA | 朱江,林建斌,徐云祥,邵学斌,蒋锡夔,&黎占亭.(2006).Hydrogen-bonding-mediated anthranilamide homoduplexes. Increasing stability through preorganization and iterative arrangement of a simple amide binding site.J. Am. Chem. Soc.,128(37),12307-12313. |
| MLA | 朱江,et al."Hydrogen-bonding-mediated anthranilamide homoduplexes. Increasing stability through preorganization and iterative arrangement of a simple amide binding site".J. Am. Chem. Soc. 128.37(2006):12307-12313. |
入库方式： OAI收割
来源：上海有机化学研究所
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