Solvent-Dependent Conformational Switching of N-Phenylhydroxamic Acid and Its Application in Crystal Engineering

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• 作者：Ryu Yamasaki ; Aya Tanatani ; Isao Azumaya ; Hyuma Masu ; Kentaro Yamaguchi ; Hiroyuki Kagechika
• 刊名：Crystal Growth & Design
• 出版年：2006
• 出版时间：September 2006
• 年：2006
• 卷：6
• 期：9
• 页码：2007 - 2010
• 全文大小：114K
• 年卷期：v.6,no.9(September 2006)
• ISSN：1528-7505

文摘

N-Phenylbenzohydroxamic acid (3) showed solvent-dependent conformational alteration. Thus, compound 3 existspredominantly in cis form (> 98%) in CD₂Cl₂, whereas the percentage of the cis isomer decreased to 49% in methanol-d₄, and thetrans conformer was major (77%) in acetone-d₆. Solvent-dependent alteration of the amide conformation was observed only in thehydroxamic acids, and the ratio of the cis conformer (98% in CD₂Cl₂) of N-phenylbenzhydrazide (6) was little affected by thesolvent. Two unique crystal structures were obtained depending on the recrystallization solvent, and each crystal corresponded instructure to the major conformer in the solvent. These two crystals of 3 were distinguished by IR spectroscopy and DSC analysis.Although the origin of the solvent-dependent conformational switching of 3 is unclear, the results could be applied to design anddevelopment of solvent- or external-stimuli-responsive molecular machines.