Generation and amplification of optical activity of axially chiral N-(1-naphthyl)-2(1H)-pyrimidinethione by crystallization.
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.
Sakamoto
Masami
M
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. sakamotom@faculty.chiba-u.jp
Yagishita
Fumitoshi
F
Ando
Masaru
M
Sasahara
Yuich
Y
Kamataki
Norifumi
N
Ohta
Mai
M
Mino
Takashi
T
Kasashima
Yoshio
Y
Fujita
Tsutomu
T