chemistry

Sulfilimine

Sulfilimine 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 Sulfilimine rather than just read about it. In short: In chemistry, a sulfilimine (or sulfimide) is a type of chemical compound containing a sulfur-to-nitrogen bond which is often represented as a double bond (S=N). In fact, a double bond violates the octet rule, and the bond may be considered a single bond with a formal charge of +1 on the sulfur and a formal charge of −1 on the nitrogen.

Key takeaways

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

Reference excerpt

In chemistry, a sulfilimine (or sulfimide) is a type of chemical compound containing a sulfur-to-nitrogen bond which is often represented as a double bond (S=N). In fact, a double bond violates the octet rule, and the bond may be considered a single bond with a formal charge of +1 on the sulfur and a formal charge of −1 on the nitrogen. The parent compound is sulfilimine H2S=NH, which is mainly of theoretical interest.

Examples include S,S-diphenylsulfilimine and sulfoximines such as methylphenylsulfoximine: In the case of a sulfoximine, the bonds can be considered single bonds, with formal charges of −1 on both the oxygen and the nitrogen, and a formal charge of +2 on the sulfur.

Preparation Most sulfilimines are N-substituted with electron-withdrawing groups. These compounds are typically prepared by oxidation of thioethers with electrophilic amine reagents, such as chloramine-T in the presence of a base:

R2S + ClNHTs → R2S=NTs + HCl An alternative route involves reactions of electrophilic sulfur compounds with amines. The imidosulfonium reagents provide a source of "Me2S2+", which are attacked by amines. In general, aliphatic sulfilimines, unsubstituted at N, are not stable above −30 °C (−22 °F). However, compounds of the form Me2S(NX)2, X a halogen, are stable well above room temperature. KMnO4 can oxidize sulfilimines to sulfoximines, but the latter are more generally produced from addition of azides to sulfoxides.

Sulfilimine bonds in proteins Sulfilimine bonds stabilize collagen IV strands found in the extracellular matrix, and evolved at least 500 mya. These bonds covalently connect hydroxylysine and methionine residues of adjacent polypeptide strands to form a larger collagen trimer.

References

Illustrations

Worked examples

Example 1 — a first encounter with Sulfilimine

Start with the simplest possible case. Write down what Sulfilimine 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 Sulfilimine 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 Sulfilimine 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 Sulfilimine

In research: Sulfilimine 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 Sulfilimine 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: Sulfilimine is common in secondary-school and first-year university syllabi. It links to neighbouring topics Functional groups, Nitrogen compounds, Sulfur compounds, so understanding it makes those chapters shorter.
In everyday life: Look for Sulfilimine 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 Sulfilimine in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Sulfilimine 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 Sulfilimine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Sulfilimine in simple terms?

Why does Sulfilimine 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 Sulfilimine?

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 Sulfilimine.