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Chapter 3: Problem 9

An isosteric series of compounds shown below, where \(\mathrm{X}=\mathrm{CH}_{2}, \mathrm{NH}, \mathrm{O}, \mathrm{S}\), was synthesized. The order of potency was \(\mathrm{X}=\mathrm{NH}>\mathrm{O}>\mathrm{S}>\mathrm{CH}_{2}\). How can you rationalize these results (you need to consider the threedimensional structure)?

Short Answer

Expert verified
Potency in the given isosteric series of compounds is rationalized based on the three-dimensional structure and specific properties of the substituents. It is believed to be determined by a consideration of factors such as the electronegativity, atom size, and the capacity to form hydrogen bonds of the substituent atoms/groups, with nitrogen displaying the highest potency due to its ability to form hydrogen bonds and its high electronegativity value.

Step by step solution

01

Analyze The Atoms in Terms of Electronegativity

The first step is to look at the electronegativity of the atoms or groups that are being substituted. Nitrogen is the most electronegative, followed by oxygen, sulfur, and finally carbon in the form of \(\mathrm{CH}_{2}\). The greater the electronegativity, the higher the biochemical potency.
02

Evaluate the Size of Atoms

The second step is to reflect on the size of the atoms and how it impacts the molecule's three-dimensional structure. The atoms increase in size from oxygen to sulfur, to nitrogen, and finally to \(\mathrm{CH}_{2}\), which is actually bigger due to the inclusion of two additional hydrogen atoms. When looking at potency, a smaller atom size could possibly lead to a more compact and effective interaction with its biological target.
03

Consider Hydrogen Bonding Capability

Next, consider the capability of atoms to form hydrogen bonds. Both nitrogen and oxygen can form hydrogen bonds, which can notably enhance the potency of a molecule due to improved interactions with the biological target. On the other hand, sulfur and \(\mathrm{CH}_{2}\) cannot form hydrogen bonds, which might explain their lower potency.
04

Compile the Information

By considering the above steps, the answer could be rationalized based on the effect the substitutions have on the interactions with possible biological targets. This interaction depends on electronegativity, ability to form hydrogen bonds and the size of the atoms or groups that are being substituted.

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