摘要
目的解析棉酚金刚烷胺Schiff碱的结构。方法制备棉酚金刚烷胺Schiff碱,并采用红外光谱,二维核磁波谱技术和PM6半经典计算方法对其结构进行分析。结果光谱分析表明棉酚金刚烷胺Schiff碱具有烯胺-烯胺结构特征并归属了所有的碳原子和氢质子的化学位移;PM6研究表明棉酚金刚烷胺Schiff碱的烯胺-烯胺和亚胺-亚胺构型的生成热分别为-1160.00kJ.mol^-1和-1008.319kJ.moL^-1,其烯胺-烯胺构型在能量上更有利。结论棉酚金刚烷胺Schiff碱以烯胺-烯胺形式存在,分子内氢键的存在使烯胺-烯胺结构更稳定。
Objective To investigate the tautomeric form of the Schiff base of gossypol with adamantanine. Methods The Schiff base of gossypol with adamantanine was synthesized and identified by FT-IR,2D-NMR Spectroscopy and the PM6 semi classical calculation.Results The 1H and 13CNMR signals of the new Schiffbase were assigned.The calculated formation heat for N-enamine-N-enamine and N-imine-N-imine tautomeric forms are-1 160.00 kJ·moL-1and-1 008.319 kJ·moL-1 respectively,indicating that the former tautomer is more stable. Conclusion The Schiff base of gossypol with adamantanine exists in enamine-enamine tautomeric form,which was stabilized by the intramolecular hydrogen bonds.
出处
《广东药学院学报》
CAS
2010年第4期358-361,共4页
Academic Journal of Guangdong College of Pharmacy
基金
国家自然科学基金(30770228)
