Why is m-Fluorophenol less acidic than all the other m-Halophenols, even though it has the most inductive effect

peter sykes 6th edition data

The data is from : A guidebook to Mechanism in organic chemistry for the JEE, 6th edition, page no. 3.12 from the chapter, the strength of acids and bases

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    $\begingroup$ What are these values in the table? $\endgroup$ Sep 10, 2023 at 18:38
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    $\begingroup$ What is the origin of the data? For one, it is to provide an easy access of the data (for future readers of the question). For two, how are the data obtained? Isolated, i.e. gas phase acidities, or in a solvent? The experimental recordings about meta chloro- or fluorophenol dissolved in DMSO for example, the Bordwell p$K_a$ table assigns both 15.8. reference. $\endgroup$
    – Buttonwood
    Sep 10, 2023 at 18:41
  • $\begingroup$ @Martin-マーチン, updated the book name, these are pka of the acids $\endgroup$ Sep 11, 2023 at 14:50
  • $\begingroup$ @Buttonwood I think it's in aqueous medium like the most of data but not sure because they haven't mentioned anything specific $\endgroup$ Sep 11, 2023 at 14:52
  • $\begingroup$ The trends are similar to Hammett sigma constants en.wikipedia.org/wiki/Hammett_equation The halogens have opposing effects electron withdrawing by induction and electron donating by resonance. Fluorine by its size seems to be more effective in the electron donation than Cl, Br I. $\endgroup$
    – jimchmst
    Sep 13, 2023 at 2:52


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