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运用量子力学PM3方法模拟α-环己基扁桃酸((R/S)-CHMA)与β-环糊精(β-CD)的主客体相互作用,探讨(R/S)-CHMA在β-CD上的手性识别机理。模拟结果能够准确预测色谱出峰顺序从而能从原子层次上对手性识别机制给予理论解释。PM3方法的计算结果表明:(S)-CHMA与β-CD形成的结合物比(R)-CHMA与β-CD形成的结合物稳定。从模拟包结物的构型可以看出(R/S)-CHMA与β-CD结合方式完全不同:(R)-CHMA是将苯环插入β-CD空腔形成包结物,而(S)-CHMA是将环己基插入β-CD空腔形成包结物。此外,(S)-CHMA除了自身的分子内氢键外,与β-CD分子之间还存在分子间氢键作用;而(R)-CHMA与β-CD之间没有分子间氢键作用。从而说明疏水作用以及弱的分子间氢键作用是造成手性识别的主要驱动力。
The interaction between α-cyclohexylmandelic acid ((R / S) -CHMA) and β-cyclodextrin (β-CD) was simulated by quantum mechanics PM3 method. On the chiral recognition mechanism. The simulation results can accurately predict the chromatographic peak order and thus can give a theoretical explanation of the chiral recognition mechanism at the atomic level. The calculation results of the PM3 method show that the conjugates formed by (S) -CHMA and β-CD are more stable than the conjugates formed by (R) -CHMA and β-CD. It can be seen from the structure of the simulated inclusion that (R / S) -CHMA completely differs from β-CD in that (R) -CHMA inserts the benzene ring into the β-CD cavity to form inclusion. ) -CHMA is a cyclohexyl group inserted into the β-CD cavity to form an entrapment. In addition, (S) -CHMA has intermolecular hydrogen bonding with β-CD except for its own intramolecular hydrogen bond, while there is no intermolecular hydrogen bonding between (R) -CHMA and β-CD. Thus, hydrophobic interaction and weak intermolecular hydrogen bonding are the main driving forces for chiral recognition.