...
  • 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Crystal growth & design >Rationalization of racemate resolution: Predicting spontaneous resolution through crystal structure prediction
【24h】

Rationalization of racemate resolution: Predicting spontaneous resolution through crystal structure prediction

机译：外消旋体拆分的合理化：通过晶体结构预测来预测自发拆分

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

Crystal structure prediction simulations are reported on 5-hydroxymethyl-2-oxazolidinone and 4-hydroxymethyl-2-oxazolidinone to establish the feasibility of predicting the spontaneous resolution of racemates of small organic molecules. It is assumed that spontaneous resolution occurs when the enantiomorph is more stable than the racemic solid. The starting point is a gas phase conformational search to locate all low-energy conformations. These conformations are used to predict the possible crystal structures of 5- and 4-hydroxymethyl-2-oxazolidinone. In both cases, the racemic crystal structure is predicted to have the lowest energy. The energy differences between the lowest-energy racemic solids and the lowest-energy enantiomorphs are 0.2 kcal mol(-1) for 5-hydroxymethyl-2-oxazolidinone and 0.9 kcal mol(-1) for 4-hydroxymethyl-2-oxazolidinone. In the case of 4-hydroxymethyl-2-oxazolidinone, where the racemic crystal is known to be more stable and the experimental crystal structures of both the racemate and the enantiomorph are available, the simulation results match the observed data. For 5-hydroxymethyl-2-oxazolidinone, where only enantiopure crystals are observed experimentally, the known experimental structure is found 1.6 kcal mol(-1) above the lowest-energy predicted structure. This work shows that it is possible to predict whether the racemate of a small chiral molecule can be resolved spontaneously, although further advances in the accuracy of lattice energy calculations are required.
机译：对5-羟甲基-2-恶唑烷酮和4-羟甲基-2-恶唑烷酮的晶体结构预测模拟进行了报道，以建立预测有机小分子外消旋物自发拆分的可行性。假定当对映体比外消旋固体更稳定时，会发生自发拆分。起点是气相构象搜索，以查找所有低能构象。这些构象用于预测5-和4-羟甲基-2-恶唑烷酮的可能晶体结构。在这两种情况下，预计外消旋晶体结构具有最低的能量。最低能量外消旋固体和最低能量对映体之间的能量差为5-k-羟甲基-2-恶唑烷酮为0.2 kcal mol（-1）和4-羟甲基-2-恶唑烷酮为0.9 kcal摩尔（-1）。在4-羟甲基-2-恶唑烷酮的情况下，已知外消旋晶体更稳定，并且可获得外消旋体和对映体的实验晶体结构，模拟结果与观察到的数据相符。对于5-羟甲基-2-恶唑烷酮，仅在实验中观察到对映体纯晶体，发现已知的实验结构比最低能量预测结构高1.6 kcal mol（-1）。这项工作表明可以预测小手性分子的外消旋体是否可以自发拆分，尽管需要进一步提高晶格能量的计算精度。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号