Synthesis and molecular structure of a chiral bipyridine-menthol ether.

Abstract

This paper presents the synthesis and structural characterization of 6,6′-bis[(1R,2S,5R)-isomenthoxy]-2,2′- bipyridine obtained by homocoupling of chiral pyridyl-ether 2-bromo-6-[(1R,2S,5R)-isomenthoxy]- pyridine. The two-step synthetic procedure afforded chiral bipyridine in a good yield and the structure of the compound is determined by X-ray diffraction. It crystallizes in a non-centrosymmetric chiral crystal structure type (P21, a = 10.7543(8) Å, b = 8.4488(6) Å, c = 15.8964(10) Å, β = 104.035(7)°, V = 1401.24(17) Å3 , Z = 2). Moreover, the compound is characterized by FTIR, high resolution mass spectrometry and its complexation capacity to transition metals is studied by UV-Vis spectroscopy.