The N-H center dot center dot center dot X (X = Cl, Br, and I) hydrogen-bonding pattern in aromatic amides: A crystallographic and H-1 NMR study | |
Zhu YY(朱元元) ; Yi HP(易会萍) ; Li C(李闯) ; Jiang XK(蒋锡夔) ; Li ZT(黎占亭) | |
刊名 | Cryst. Growth Des.
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2008 | |
卷号 | 8期号:4页码:1294-1300 |
ISSN号 | 1528-7483 |
其他题名 | 芳酰胺内的N-H...X (X = Cl, Br 和 I)氢键:晶体及核磁共振研究 |
通讯作者 | 黎占亭 |
英文摘要 | This paper addresses the stability of the intramolecular five- and six-membered N-H center dot center dot center dot X (X = Cl, Br, and I) hydrogen bonds in aromatic amides. The crystal structures of 11 chloro-, bromo-, or iodo- substituted aromatic amides are reported. It is revealed that five-membered N-H center dot center dot center dot X hydrogen bonding occurs for all the halogen atoms in the designed compounds. Introduction of a large aryl or alkyl unit increases the stability of the hydrogen bonding because its existence weakens the competitive intermolecular N-H center dot center dot center dot O=C hydrogen bonding. A stable six-membered N-H center dot center dot center dot Cl hydrogen bond is also exhibited in the crystal structure of N-triphenylmethyl 2-chlorobenzamide. However, its bromo- and iodo- substituted counterparts display only intermolecular N-H center dot center dot center dot O=C hydrogen bonding. H-1 NMR experiments in CDCl3 for 18 halogenated isomeric N -phenyl benzamides indicate that in solution five-membered N-H center dot center dot center dot X (X = Cl, Br, and I) hydrogen bonds can also be formed, but no evidence for the existence of the six-membered one is observed. The results show that the five-membered N-H center dot center dot center dot X (X = Cl, Br, and I) hydrogen bond is generally more stable than its corresponding six-membered counterpart. |
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/cg7010293 |
语种 | 英语 |
WOS记录号 | WOS:000254649300038 |
公开日期 | 2013-01-16 |
内容类型 | 期刊论文 |
源URL | [http://202.127.28.38/handle/331003/12750] ![]() |
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 YY,Yi HP,Li C,et al. The N-H center dot center dot center dot X (X = Cl, Br, and I) hydrogen-bonding pattern in aromatic amides: A crystallographic and H-1 NMR study[J]. Cryst. Growth Des.,2008,8(4):1294-1300. |
APA | 朱元元,易会萍,李闯,蒋锡夔,&黎占亭.(2008).The N-H center dot center dot center dot X (X = Cl, Br, and I) hydrogen-bonding pattern in aromatic amides: A crystallographic and H-1 NMR study.Cryst. Growth Des.,8(4),1294-1300. |
MLA | 朱元元,et al."The N-H center dot center dot center dot X (X = Cl, Br, and I) hydrogen-bonding pattern in aromatic amides: A crystallographic and H-1 NMR study".Cryst. Growth Des. 8.4(2008):1294-1300. |
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