Tetrahedron letters

17O NMR spectroscopy: Unusual substituent effects in para-substituted benzyl alcohols and acetates

P Balakrishnan, AL Baumstark, DW Boykin

Index: Balakrishnan, P.; Baumstark, A. L.; Boykin, D. W. Tetrahedron Letters, 1984 , vol. 25, # 2 p. 169 - 172

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Citation Number: 33

Abstract

The 17 O chemical shifts for para-substituted benzyl alcohols and acetates were measured: electron donating substituents resulted in deshielding and electron withdrawing groups resulted in shielding of the chemical shift; the data are correlated by DSP treatment. ... Correlation with σ and σ + for acetates and alcohols in acetone are comparable: alcohols SCS=−7.78 σ + 0.487, SD=0.60, r=0.989; SCS=−4.99 σ + − 0.76, SD=0.71, r=0.984; acetates SCS=−8.34 σ + ...