N-H…X(X=F,Cl,Br,and Ⅰ)hydrogen bonding in aromatic amide derivatives in crystal structures  

作　　者：WANG DongYun WANG JiLiang ZHANG DanWei LI ZhanTing 

机构地区：[1]Department of Chemistry,Fudan University,Shanghai 200433,China

出　　处：《Science China Chemistry》2012年第10期2018-2026,共9页中国科学（化学英文版）

基　　金：the National Natural Science Foundation of China (21172042and 20974118);the Ministry of Education of China (IR1117) for financial support

摘　　要：Intramolecular N H···X (X=F, Cl, Br, and Ⅰ) hydrogen bonding patterns of aromatic amides in the solid state are summarized. It is revealed that the key for the formation of this kind of weak intramolecular hydrogen bonding in X-ray crystal structures is to suppress the competition of strong intermolecular N H···O C hydrogen bonding of the amide unit. For amides with identical backbones, the bonding capacity of halogen atoms as hydrogen bonding acceptors is in the order of F>Cl>Br>I, which is in accordance with their electronegativity strength. Generally, the five-membered hydrogen bonding is easier to form than the six-membered one.Intramolecular N H···X （X=F, Cl, Br, and Ⅰ） hydrogen bonding patterns of aromatic amides in the solid state are summarized. It is revealed that the key for the formation of this kind of weak intramolecular hydrogen bonding in X-ray crystal structures is to suppress the competition of strong intermolecular N H···O C hydrogen bonding of the amide unit. For amides with identical backbones, the bonding capacity of halogen atoms as hydrogen bonding acceptors is in the order of FClBrI, which is in accordance with their electronegativity strength. Generally, the five-membered hydrogen bonding is easier to form than the six-membered one.

关 键 词：hydrogen bond halogen acceptor aromatic amide X-ray crystallography 

分 类 号：O623.413[理学—有机化学] TQ464.71[理学—化学]