Chq

a-Amino acid (glycine)

pKa = 9.60 Electronegative oxygen atoms in the carboxyl group pull electrons away from the amino group, lowering its pKa.

FIGURE 3-11 Effect of the chemical environment on pKa. The pKa values for the ionizable groups in glycine are lower than those for simple, methyl-substituted amino and carboxyl groups. These downward perturbations of pKa are due to intramolecular interactions. Similar effects can be caused by chemical groups that happen to be positioned nearby—for example, in the active site of an enzyme.

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