title: Generation and amplification of optical activity of axially chiral N-(1-naphthyl)-2(1H)-pyrimidinethione by crystallization.
abstract: 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.
authors.affiliation: 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
authors.forename: Masami
authors.initials: M
authors.lastname: Sakamoto
authors.forename: Fumitoshi
authors.initials: F
authors.lastname: Yagishita
authors.forename: Masaru
authors.initials: M
authors.lastname: Ando
authors.forename: Yuich
authors.initials: Y
authors.lastname: Sasahara
authors.forename: Norifumi
authors.initials: N
authors.lastname: Kamataki
authors.forename: Mai
authors.initials: M
authors.lastname: Ohta
authors.forename: Takashi
authors.initials: T
authors.lastname: Mino
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Kasashima
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Fujita