Chiral self-discrimination of the enantiomers of alpha-phenylethylamine derivatives in proton NMR.
Two types of chiral analytes, the urea and amide derivatives of alpha-phenylethylamine, were prepared. The effect of inter-molecular hydrogen-bonding interaction on self-discrimination of the enantiomers of analytes has been investigated using high-resolution (1)H NMR. It was found that the urea derivatives with double-hydrogen-bonding interaction exhibit not only the stronger hydrogen-bonding interaction but also better self-recognition abilities than the amide derivatives (except for one bearing two NO(2) groups). The present results suggest that double-hydrogen-bonding interaction promotes the self-discrimination ability of the chiral compounds.
Huang
Shao-Hua
SH
State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Institute of Physics and Mathematics, the Chinese Academy of Sciences, Wuhan 430071, China.
Bai
Zheng-Wu
ZW
Feng
Ji-Wen
JW
D000577:Amides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009566:Nitrates / Q000737:chemistry; D010627:Phenethylamines / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry
D000577:Amides; D009566:Nitrates; D010627:Phenethylamines; D011522:Protons; D014508:Urea; C033198:1-phenethylamine