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Which functional group on furosemide's structure below is most likely to be negatively charged at physiological pH (7.4)?

Which functional group on furosemide's structure below is most likely to be negatively charged at physiological pH (7.4)?

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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**Question 3: Which functional group on furosemide’s structure below is most likely to be negatively charged at physiological pH (7.4)?** The image features the chemical structure of furosemide. Furosemide contains various functional groups within its structure, including: 1. A sulfonamide group with the sulfur atom double-bonded to two oxygen atoms and single-bonded to a nitrogen (SO2NH2). 2. A chlorine atom attached to an aromatic ring. 3. A carboxylic acid group (COOH) attached to an aromatic ring. **Explanation:** At physiological pH (7.4), the carboxylic acid group is most likely to be negatively charged. This is due to the deprotonation of the hydrogen ion from the hydroxyl group, forming the carboxylate ion (COO⁻). Understanding these properties is crucial for predicting the solubility, distribution, and mechanism of action of furosemide in biological systems.
Transcribed Image Text:**Question 3: Which functional group on furosemide’s structure below is most likely to be negatively charged at physiological pH (7.4)?** The image features the chemical structure of furosemide. Furosemide contains various functional groups within its structure, including: 1. A sulfonamide group with the sulfur atom double-bonded to two oxygen atoms and single-bonded to a nitrogen (SO2NH2). 2. A chlorine atom attached to an aromatic ring. 3. A carboxylic acid group (COOH) attached to an aromatic ring. **Explanation:** At physiological pH (7.4), the carboxylic acid group is most likely to be negatively charged. This is due to the deprotonation of the hydrogen ion from the hydroxyl group, forming the carboxylate ion (COO⁻). Understanding these properties is crucial for predicting the solubility, distribution, and mechanism of action of furosemide in biological systems.
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