Problem

Solutions For An Introduction to Medicinal Chemistry Chapter 11 Problem 5Q

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Solution 1

The power of dissociation of an acid or base refers to the negative of the logarithm of their equilibrium dissociation constant. Hence, if the equilibrium constant for a dissociation reaction is Ka:

The power of hydrogen, or pH, relative to the pK of a solution will determine the extent of ionization of an acidic or basic solution. The extent of ionization of histamine will depend upon the pH of its surrounding solution.

(a)

If the pH value of a histamine solution is 5.74, it is at equilibrium in its dissociation reaction. Hence, the ratio of ionized to unionized histamine will be 1:1.

(b)

If the pH value of histamine solution is 7.4, which means that the solution is more basic than pKa of histamine. Hence, there will be a higher degree of unionized histamine relative to ionized histamine. As per the Henderson-Hasslebach equation:

Upon substituting the values

Hence, the ratio of ionized to non-ionized histamine will amount to approximately.

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