Mechanisms Underlying Enantiomeric Discrimination of Its Structural Analogues with a Diphenylethylenediamine Derivative Revealed by Proton NMR Spectroscopy

doi:10.11938/cjmr20182703

Abstract

Abstract: A C₂-symmetric host (host 1) was synthesized by derivatization of chiral diphenylethylenediamine with phenylisocyanate. High-resolution proton nuclear magnetic resonance (¹H NMR) was used to investigate whether the chiral host could be used for enantiomeric discrimination of its structural analogues:α-phenylethylamine (guest 2), α-(p-methoxyphenyl)ethylamine (guest 9) and their derivatives (guests 3~8 and 10~13), and hydrogen-bonding interactions underlying the enantiomeric discrimination. It was observed that the host was able to recognize the urea and amide derivatives of the two primary amines, except for guests 7 and 12 bearing two NO₂ groups. The host had stronger hydrogen-bonding interactions with the urea derivatives of guests 2 and 9 than with the corresponding amide derivatives, and high enantiomeric discrimination ability for the CHCH₃ groups of the (R)- and (S)-urea derivatives.

Key words: diphenylethylenediamine, derivative, enantiomeric discrimination, nuclear magnetic resonance (NMR) spectroscopy

CLC Number:

O482.53

YANG Ying, HUANG Shao-hua, FENG Ji-wen. Mechanisms Underlying Enantiomeric Discrimination of Its Structural Analogues with a Diphenylethylenediamine Derivative Revealed by Proton NMR Spectroscopy[J]. Chinese Journal of Magnetic Resonance, 2019, 36(4): 525-533.

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