Modulation of Conformational Preferences of Heteroaromatic Ethers and Amides through Protonation and Ionization: Charge Effect
文献类型：期刊论文
| 作者 | Dai, Wenshuai1,2; Zhang, Zhe1,2; Du, Yikui1 |
| 刊名 | CHEMISTRYOPEN
 |
| 出版日期 | 2019-07-01 |
| 卷号 | 8期号:7页码:840-851 |
| ISSN号 | 2191-1363 |
| 关键词 | conformational modulation heteroaromatic ethers heteroaromatic amides protonation ionization |
| DOI | 10.1002/open.201900103 |
| 通讯作者 | Du, Yikui(ydu@iccas.ac.cn) |
| 英文摘要 | Multiple approaches reveal the strong effects of a positive charge introduced by protonation or ionization on the conformation of o-heteroaromatic ethers and amides. The ethers and amides containing an ortho-N heteroatom are syn-preferring while those containing an ortho-O or ortho-S heteroatom are mostly anti-preferring. However, for all the monocyclic o=heteroaromatic ethers and amides, the protonated ones are all anti-preferring while the ionized ones are all syn-preferring. Interestingly, although both the protonation and ionization introduce a positive charge, they have such different effects on molecular conformation, very informative for understanding the origin of conformational preferences. Detailed analysis shows that the population of the introduced positive charge dictates the conformational preferences via electrostatic and orbital interactions. Compared to ortho-heteroatoms, meta-heteroatoms have weaker effect on conformational preference. Achieved by complete inductive method, the regularity of conformational preferences and switching provides easy ways to modulate conformers (by pH or redox), and makes this kind of ether or amide bond a conformational hinge applicable to design of functional molecules (drugs and materials) and modulation of molecular biological processes. |
| WOS关键词 | 2-METHOXYPYRIDINE ; DENSITY ; ISOMERIZATION ; SIGNATURE ; DISCOVERY ; POTENT ; NMR |
| 资助项目 | National Natural Science Foundation of China[20973180] ; National Natural Science Foundation of China[21190034] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| WOS记录号 | WOS:000477965100005 |
| 资助机构 | National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/173703]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 通讯作者 | Du, Yikui |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, State Key Lab Mol React Dynam, Beijing 100190, Peoples R China 2.Univ Chinese Acad Sci, Sch Chem Engn, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Dai, Wenshuai,Zhang, Zhe,Du, Yikui. Modulation of Conformational Preferences of Heteroaromatic Ethers and Amides through Protonation and Ionization: Charge Effect[J]. CHEMISTRYOPEN,2019,8(7):840-851. |
| APA | Dai, Wenshuai,Zhang, Zhe,&Du, Yikui.(2019).Modulation of Conformational Preferences of Heteroaromatic Ethers and Amides through Protonation and Ionization: Charge Effect.CHEMISTRYOPEN,8(7),840-851. |
| MLA | Dai, Wenshuai,et al."Modulation of Conformational Preferences of Heteroaromatic Ethers and Amides through Protonation and Ionization: Charge Effect".CHEMISTRYOPEN 8.7(2019):840-851. |
入库方式： OAI收割
来源：大连化学物理研究所
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。