Page 110 - Medicinal Chemistry Self Assessment
P. 110
Section 3 General Self Assessment Answers
2.2 Identifying Acidic and Basic
2.2
Functional Groups
1. For each of the drugs or experimental drugs shown below, identify all of the acidic and basic functional
groups.
1. For each of the drugs or experimental drugs shown below, identify all of the acidic and basic functional
groups.
Answer
2 3
1
4
Experimental oral anticoagulant Bromfenac
5
7
8
6
Sorbinil
Experimental antidiabetic agent
Answer:
Drug Name Acidic Functional Groups Basic Functional Groups
As discussed in Chapter 3*, there are two key structural features of an acidic functional group. The first is the
Experimental Oral Anticoagulant Sulfonamide (2) Amidine (1)
+
presence of a proton (H ) that can leave (i.e., dissociate), and the second is the presence of adjacent atoms that
Bromfenac Carboxylic acid (4) Aromatic amine or aniline (3)
acid and an imide are acidic, while functional groups such as secondary hydroxyl groups (i.e., secondary
Sorbinil Imide (5) None
Experimental Antidiabetic Agent Phenol (6) Secondary amine (8)
alcohols) and thiols are neutral functional groups.
Sulfonamide (7)
Resonance stabilization No resonance available
of resulting negative charge if proton would leave
99
Carboxylic Secondary Sulfhydryl
Acid Imide Hydroxyl
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