Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Org Biomol Chem. 2010 Dec 7;8(23):5418-22. doi: 10.1039/c0ob00262c. Epub 2010 Sep 24.
X-Ray crystallographic analysis of N-(1-naphthyl)-2(1H)-pyrimidinethione revealed that the space group was tetragonal and chiral P4(3). The rate of racemization due to the C-N bond rotation was considerably influenced by the solvent properties. A nonpolar solvent lowers the ΔG(‡)value by about 3.0 kcal mol(-1) relative to the value in a polar or a protic solvent. The crystallization of racemic axially chiral pyrimidinethione at high temperature led to the chiral breaking of symmetry up to 91% ee.
X 射线晶体学分析表明，N-(1-萘基)-2(1H)-嘧啶硫酮属于四方晶系和手性 P4(3)空间群。由于 C-N 键的旋转，外消旋化的速度受到溶剂性质的极大影响。与极性或质子性溶剂相比，非极性溶剂使 ΔG(‡)值降低约 3.0 kcal mol(-1)。在高温下，外消旋轴手性嘧啶硫酮的结晶导致了高达 91%ee 的手性对称破缺。
