Conformational analysis of methyl 2-methyl-2-(1-naphthyl)propionate

Takatoshi Matsumoto, Yoshio Kinoshita, Yusuke Kasai, Shunsuke Kuwahara, Masataka Watanabe

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

(S)-2-Methoxy-2-(1-naphthyl)propionic acid (MαNP acid 1) is used for enantioseparation of many secondary alcohols and for determining the stereogenic centers. In the liquid state, based on the 1H NMR anisotropy effect and reported results, it was shown that the MαNP ester preferred a coplanar relation between the methyl and naphthyl groups and a synperiplanar relation between the Cα-OMe and C{double bond, long}O groups. In the case of 1,2,3,4-tetrahydro-4-phenanthrenol, which is a secondary alcohol, the stereogenic center was determined by X-ray analysis. It was shown that MαNP ester adopted similar arrangements in the solid state. However, it was presumed that the strong repulsion between oxygen atoms may be disadvantageous in the solid state. Therefore, we carried out conformational analysis using the simplest MαNP methyl ester to clarify this unique relationship. From detailed results based on the energy surface determined using the RHF/STO-3G basis set, the synperiplanar positional relation was the most stable, and the calculated results agreed with many reported experimental results. At the same time, all conformational isomers of the MαNP methyl ester were used to clarify the internal conversion pathways.

Original languageEnglish
Pages (from-to)615-624
Number of pages10
JournalTetrahedron
Volume63
Issue number3
DOIs
Publication statusPublished - 2007 Jan 15

Keywords

  • Ab initio
  • Conformational analysis
  • Energy surface
  • Internal conversion pathway
  • MαNP methyl ester

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Conformational analysis of methyl 2-methyl-2-(1-naphthyl)propionate'. Together they form a unique fingerprint.

  • Cite this