Computational study of Simultaneous synthesis of optically active (RS)-1,2,4-butanetriol trinitrate (BTTN)

作者：Liu Min Hsien^*; Tsai Hou Jen; Liu Chuan Wen

来源：Journal of Molecular Modeling, 2017, 23(8): 246.

DOI：10.1007/s00894-017-3414-9

• Polarizable continuum model (PCM)
• Aldol condensation
• Simultaneous reaction
• Optically active
• (RS)-1,2,4-butanetriol trinitrate
• Temperature effect

In respective water or ethanol polarizable continuum cavity environments, simultaneous aldol condensation was performed using density functional theory (DFT) computational method to model the synthesis of optically active (RS)-1,2,4-butanetriol trinitrate (BTTN). The results of reaction energy barrier analysis suggested feasible routes with lower activation energies to obtain either the (R)- or (S)-configuration product in ethanolic solution. In addition, local analysis of average inter-particulate distances of reaction species revealed that a stronger inter-particulate interaction accompanied a shorter average distance in the ethanol system. The stabilization effect also indicated that related syntheses would be able to proceed in ethanol. Furthermore, relative to the production of (R)-BTTN, a lower overall energy of 425.3 kJ/mol was required for the synthesis of (S)-BTTN. Through analysis of the effects of temperature on the reaction rates of individual parallel stages of (R)-and (S)-species synthesis, it was simple to adjust the reaction temperature accordingly to differentiate between relative rates in order to obtain a product of a specific configuration.

• 出版日期2017-8
• 单位中国人民解放军国防大学