Page 112 - Medicinal Chemistry Self Assessment
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For basic functional groups, the key structural feature is a nitrogen atom that has a lone pair of nonbonding
amides are not.
Resonance with
adjacent carbonyl greatly
Amidine Secondary decreases availablity of electrons
amine Amide
2.2 Identifying Acidic and Basic Functional Groups 101
3. Using the structures from question 1, modify all of the acidic functional groups to show their ionized forms and
in the table below identify the normal pKa range for the specific functional group.
3. Using the structures from question 1, modify all of the acidic functional groups to show their ionized
forms and in the table below identify the normal pK range for the specific functional group.
Answer: a
Answer
_
Experimental oral anticoagulant Bromfenac
_
Sorbinil
Experimental antidiabetic agent
Drug Name Acidic Functional Group Normal pK Range
a
Experimental Oral Anticoagulant Sulfonamide pK =5 to 10
a
Bromfenac Carboxylic acid pK =2.5 to 5
a
Sorbinil Imide pK =4.5 to 8.5 (generally on the higher end,
7.0 to 8.5)
a
Experimental Antidiabetic Agent Phenol pK =9 to 10
a
Sulfonamide pK =5 to 10
a
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