example of different charge stabilization factors

Acetic acid (ethanoic acid) has a pKa of approximately 4.7. If the OH is replaced with an SH, then the pKa drops to 3.4 because of a size effect. Placement of the charge on a larger sulfur atom is more favorable than oxygen. If the CH3 group of acetic acid is given a chlorine atom, then the pKa drops to 2.9 because of the inductive effect. The polarized C-Cl bond places a partial positive charge on the carbon, which stabilized the neighboring O minus.

organic chemistry,charge stabilization,acetic acid,thioacetic acid,chloroacetic acid,inductive effect,induction,size,