Mesomeric effect

The effect is responsible for stability greater than that predicted. It affects the stability of compounds by resonating the electrons/charge over the molecule. Thus it can stabilise the anion formed after the loss of a proton, making the compound more acidic. Additionally, the effect of delocalising the electrons and therefore the charge, will reduce the probability of the anion being reprotonated as it is now a "soft nucleophile" (disperse charge) compared to the "hard electrophile" of the proton (small localised charge).

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It's important to note that the mesomeric affect as a result of p - orbital overlap has absolutely no affect on the inductional effect, as this effect is purely to do with the electronegativity of the atoms and their structural chemistry (which atoms are connected to which).

Related Topics:
Inductional effect - Electronegativity

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