2012
DOI: 10.1002/mrc.3864
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17O NMR studies of ortho‐substituent effects in substituted phenyl tosylates

Abstract: (17)O NMR spectra for 35 ortho-, para-, and meta-substituted phenyl tosylates (phenyl 4-methylbenzenesulfonates), 4-CH(3)-C(6)H(4) SO(2)OC(6)H(4)-X, at natural abundance in acetonitrile at 50 °C were recorded. The (17)O NMR chemical shifts, δ((17)O), of the sulfonyl (SO(2)) and the single-bonded phenoxy (OPh) oxygens for para and meta derivatives correlated well with dual substituent parameter treatment using the Taft inductive, σ(I), and resonance, σº(R), constants. The influence of ortho substituents on the … Show more

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Cited by 4 publications
(23 citation statements)
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References 52 publications
(83 reference statements)
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“…The preparation procedure and characteristics for the most ortho ‐substituted, meta ‐substituted, and para ‐substituted phenyl esters of para ‐toluenesulfonic acid, 4‐CH 3 ‐C 6 H 4 SO 2 OC 6 H 4 ‐X, used in the present work have been described previously …”
Section: Methodsmentioning
confidence: 99%
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“…The preparation procedure and characteristics for the most ortho ‐substituted, meta ‐substituted, and para ‐substituted phenyl esters of para ‐toluenesulfonic acid, 4‐CH 3 ‐C 6 H 4 SO 2 OC 6 H 4 ‐X, used in the present work have been described previously …”
Section: Methodsmentioning
confidence: 99%
“…Previously, the influence of substituent effects on the 17 O NMR chemical shifts, δ ( 17 O), of the sulfonyl (SO 2 ) oxygen and single‐bonded phenoxy (PhO) oxygen in substituted phenyl tosylates has been studied in the case of neutral (uncharged) substituents in CH 3 CN. In the present paper, DMSO was used as solvent because the solubility of phenyl tosylates with charged substituents in CH 3 CN is too low for recording the 17 O NMR spectra.…”
Section: Introductionmentioning
confidence: 99%
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