Journal
TETRAHEDRON LETTERS
Volume 54, Issue 21, Pages 2571-2574Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.02.110
Keywords
Ionization constant; Phenols; H-1 NMR; Hammett-Taft; pK(a) Prediction
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Simple empirical correlations were proposed between phenol pK(a) in various solvents (H2O, DMF, CH3CN, DMSO, and i-PrOH) and their chemical shifts delta(OH) measured in DMSO-d(6). The following method permits to predict pKa values for most phenols in the studied solvents with a good accuracy when intramolecular interactions (hydrogen bonds, steric hindrance, and tautomeric resonance) can be neglected. To illustrate the scope of the method we applied it to nine complex monoprotic phenols for which Hammett substituent constants sigma(-) were not compiled. The results obtained in water were in good agreement with the results obtained from ACD/pK(a) software and allowed to extend the calculation to their sigma(-) Hammett substituent constants and pK(a), values in other solvents. (C) 2013 Elsevier Ltd. All rights reserved.
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