Comparison of hydrogen bonding for chiral and racemic 1-monostearoylglycerols in solvent.
Comparison of the hydrogen bonding of racemic RS-1-monostearoylglycerol and chiral S-1-monostearoylglycerol in benzene was carried out through the NMR measurement. In addition, the concentration dependence of a chirality of S-1-monostearoylglycerol in hexane was studied though UV and circular dichroism (CD) measurements. The chemical shifts of OH protons of the S- and RS-1- monostearoylglycerols indicated that the hydrogen bonding between the R- and S-form molecules of RS-1-monostearoylglycerol is stronger than that between the S- and S-form molecules of S-1-monostearoylglycerol in the low concentration region and that the difference in the strength of hydrogen-bonding between them becomes small in the high concentration region. The chirality of the S-1-monostearoyglycerol in hexane decreased with increasing its concentration. This suggests that the association of chiral S-1-monoacylglycerol arising from its increasing concentration reduces the chirality of S-1-monostearoylglycerol.
Matsuzawa
Hideyo
H
Department of Chemistry, School of Science, Kitasato University, Sagamihara, Kanagawa-ken, Japan. matsu@sci.kitasato-u.ac.jp
Murakami
Kiyofumi
K
Iwahashi
Makio
M
D016880:Anisotropy; D001554:Benzene / Q000737:chemistry; D002942:Circular Dichroism; D006586:Hexanes / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D012997:Solvents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013228:Stearates / Q000737:chemistry*; D013237:Stereoisomerism
D006586:Hexanes; D012997:Solvents; D013228:Stearates; D001554:Benzene