1H NMR Studies on Synthetic Isoflavones with p-Substituents on B Ring

Abstract

Abstract: In this paper, ¹H NMR study on fourteen isoflavones with various p substituents on B ring is reported. The effects of substituents on the chemical shifts of A, B and C ring protons are discussed. Unambiguous assignments of unsubstituted B ring ¹H resonance spectra were made with the aid of superconductive NMR spectroanalysis. There is a linear relationship between the chemical shifts of B ring protons and the substituent parameters. The chemical shifts of 2'(6')-¹H and 3'(5')-¹H show a linear correlation with Hammett constants σ_p and substituent parameter S₀ respectively. The resonance shifts of 3'(5')-¹H arise from the electron and magnetic anisotropy effects, while the resonance shifts of 2'(6')-¹H respond to the electron effects of the substituents primarily.

Key words: Isoflavones, ¹H NMR, Resonance shift

CLC Number:

O657.36

TrendMD:

LIU Peng, CHEN Rong-Feng, CHANG Jun-Biao, XIE Jing-Xi . ¹H NMR Studies on Synthetic Isoflavones with p-Substituents on B Ring[J]. Chem. J. Chinese Universities, 2000, 21(11): 1671.

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¹H NMR Studies on Synthetic Isoflavones with p-Substituents on B Ring

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