Stereoelectronic effects on 1H nuclear magnetic resonance chemical shifts in methoxybenzenes

…, L Olsen, JW Jaroszewski

Index: Lambert, Maja; Olsen, Lars; Jaroszewski, Jerzy W. Journal of Organic Chemistry, 2006 , vol. 71, # 25 p. 9449 - 9457

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Citation Number: 9

Abstract

Investigation of all O-methyl ethers of 1, 2, 3-benzenetriol and 4-methyl-1, 2, 3-benzenetriol (3-16) by 1H NMR spectroscopy and density-functional calculations disclosed practically useful conformational effects on 1H NMR chemical shifts in the aromatic ring. While the conversion of phenol (2) to anisole (1) causes only small positive changes of 1H NMR chemical shifts (Δδ< 0.08 ppm) that decrease in the order Hortho> Hmeta> Hpara, the ...