chemistry

Oxathiazolones

Oxathiazolones is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Oxathiazolones rather than just read about it. In short: The oxathiazolones are a family of heterocyclic compounds in which the parent derivative has the molecular formula C2HNO2S and for which multiple isomers are known. The two known isomers with the highest profile in the literature are 1,3,4-oxathiazol-2-one and 1,4,2-oxathiazol-5-one. 1,3,4-Oxathiazol-2-one Molecular and electronic structure 1,3,4-Oxathiaol-2-one derivatives are planar heterocycles that prefer co-pla…

Key takeaways

Oxathiazolones belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Oxathiazolones to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Oxathiazolones from memory before moving on to harder problems.

Reference excerpt

The oxathiazolones are a family of heterocyclic compounds in which the parent derivative has the molecular formula C2HNO2S and for which multiple isomers are known. The two known isomers with the highest profile in the literature are 1,3,4-oxathiazol-2-one and 1,4,2-oxathiazol-5-one.

1,3,4-Oxathiazol-2-one

Molecular and electronic structure 1,3,4-Oxathiaol-2-one derivatives are planar heterocycles that prefer co-planarity with aromatic substituents. It has been proposed that the π system of the ring consists of CNS and CO2 "π islands" that prefer coplanarity to enhance inter-ring π conjugation.

Synthesis The traditional route for 1,3,4-oxathiazol-2-one synthesis is via 1,3 dipolar cycloaddition, where chlorocarbonylsulfenyl chloride and amide are heated together in an appropriate solvent. Appropriate solvents must dissolve the amide. Typically toluene or chloroform is used. A wide variety of amides have been used is the synthesis of 1,3,4-oxathiazol-2-one yielding various derivatives. Variations in this procedure have included doing the reaction under an inert atmosphere, adding chlorocarbonylsulfenyl chloride drop-wise, and varying the ratio of chlorocarbonylsulfenyl chloride to amide. Variations in procedure may be due to local preferences or substituent effects.

Reactions

Decarboxylation leading to isothiazole derivatives 1,3,4-Oxathiazol-2-one derivatives are commonly used in thermal decarboxylation reactions to generate the corresponding derivative of the short-lived nitrile sulfide which may be trapped by 1,3-dipolar cycloaddition reactions to give heterocycles in low to high yields depending on the nature of the substituent groups.

The intermediate can be trapped with a suitable electron deficient dipolarophile to give stable heterocycles such as isothiazole (seen below).

Other decarboxylation reactions The intermediate has been successfully trapped using other dipolarophiles including nitriles, alkenes, and phosphaalkenes.

Biological significance and applications Some 1,3,4-oxathiazol-2-one heterocycles have demonstrated selective inhibition of proteasomes in Mycobacterum tuberculosis and humans. Oxathiazolones HT1171 and GL5 (right) selectively inhibited the M. tuberculosis 26S proteasome and were over 1000-fold less effective on the human proteasome even in high concentrations. Various 5‐styryl‐oxathiazol‐2‐one heterocycles have also been tested as anti-tubercular agents because of their ability to inhibit the M. tuberculosis 26S proteasome. A Bortezomib derived 1,3,4-oxathiazol-2-one (bort(L)-oxathiazol-2-one, right) selectively acts against the human proteasome rather than bacterial proteasomes, much like Bortezomib. HT2210 and HT2106 (right) were found to have similar effects. Human proteasome inhibition is useful in the treatment of cancer, neurodegenerative disorders, and inflammation.

See also Oxazolone, an analog without the sulfur atom. Thiazole and isothiazole, analogues without the carbonyl group or oxygen atom. Oxazole and isoxazole, analogues without the carbonyl group or sulfur atom.

References

Illustrations

Worked examples

Example 1 — a first encounter with Oxathiazolones

Start with the simplest possible case. Write down what Oxathiazolones claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Oxathiazolones before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Oxathiazolones ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Oxathiazolones

In research: Oxathiazolones appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Oxathiazolones in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Oxathiazolones is common in secondary-school and first-year university syllabi. It links to neighbouring topics Nitrogen heterocycles, Organic compounds with 2 carbon atoms, Oxygen heterocycles, so understanding it makes those chapters shorter.
In everyday life: Look for Oxathiazolones outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Oxathiazolones in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Oxathiazolones means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Oxathiazolones out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Oxathiazolones in simple terms?

Why does Oxathiazolones matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Oxathiazolones?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Oxathiazolones.