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orthocresol
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Why isn't ortho isomerdoes sulfonation of aminobenzenesulfonic acid a major productaniline occur para rather than ortho?

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orthocresol
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In the second paragraph of the image you can see that p-aminobenzenesulfonic acid is more stableAccording to a textbook by K. L. Chugh:

In the second paragraph of the image you can see that p-amino-benzenesulphonic acid is more stable.

Sulfonation [of aniline] is a reversible reaction. The p-isomer, being more stable, does not get desulfonated easily. Hence, p-sulfanilic acid is the major product.

But accordingI am curious as to me,why the oortho isomer (2-aminobenzenesulfonic acid should be) is not more thermodynamically stable as there. There is six-member cyclea possibility of Hintramolecular hydrogen bonding (in a six-bonding.membered ring):

Intramolecular hydrogen bond in 2-aminobenzenesulfonic acid

Am I wrong in my claimWhy is the para isomer (4-aminobenzenesulfonic acid) favoured?

In the second paragraph of the image you can see that p-aminobenzenesulfonic acid is more stable.

In the second paragraph of the image you can see that p-amino-benzenesulphonic acid is more stable.

But according to me, o-aminobenzenesulfonic acid should be more stable as there is six-member cycle of H-bonding.

Am I wrong in my claim?

According to a textbook by K. L. Chugh:

Sulfonation [of aniline] is a reversible reaction. The p-isomer, being more stable, does not get desulfonated easily. Hence, p-sulfanilic acid is the major product.

I am curious as to why the ortho isomer (2-aminobenzenesulfonic acid) is not more thermodynamically stable. There is a possibility of intramolecular hydrogen bonding (in a six-membered ring):

Intramolecular hydrogen bond in 2-aminobenzenesulfonic acid

Why is the para isomer (4-aminobenzenesulfonic acid) favoured?

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user7951
user7951

In the second paragraph of the image you can see that p-aminobenzenesulfonic acid is more stable.

In the second paragraph of the image you can see that p-amino-benzenesulphonic acid is more stable.In the second paragraph of the image you can see that p-amino-benzenesulphonic acid is more stable.

But according to me, o-aminobenzenesulfonic acid should be more stable as there is six-member cycle of H-bonding.

Am I wrong in my claim?

In the second paragraph of the image you can see that p-aminobenzenesulfonic acid is more stable.

In the second paragraph of the image you can see that p-amino-benzenesulphonic acid is more stable.

But according to me, o-aminobenzenesulfonic acid should be more stable as there is six-member cycle of H-bonding.

Am I wrong in my claim?

In the second paragraph of the image you can see that p-aminobenzenesulfonic acid is more stable.

In the second paragraph of the image you can see that p-amino-benzenesulphonic acid is more stable.

But according to me, o-aminobenzenesulfonic acid should be more stable as there is six-member cycle of H-bonding.

Am I wrong in my claim?

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user7951
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