chemistry

Organoantimony chemistry

Organoantimony chemistry 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 Organoantimony chemistry rather than just read about it. In short: Organoantimony chemistry is the chemistry of compounds containing a carbon to antimony (Sb) chemical bond. Relevant oxidation states are SbV and SbIII.

Key takeaways

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

Reference excerpt

Organoantimony chemistry is the chemistry of compounds containing a carbon to antimony (Sb) chemical bond. Relevant oxidation states are SbV and SbIII. Few applications have been reported for this class of compounds. They are of interest as heavy analogues of organophosphorus compounds.

Antimony(III) derivatives

Synthesis Stibines are typically prepared by alkylation of antimony trichloride with organolithium or Grignard reagents:

SbCl3 + 3 RLi (or RMgCl) → R3Sb Triphenylstibine (triphenylantimony) is one of the best studied organoantimony compounds and representative of the entire class of stibines. 1-Phenylstibole, a relative of pyrrole, can be prepared by treating 1,4-dilithiobutadiene with phenyldichlorostibine:

LiCH=CH−CH=CHLi + PhSbCl2 → H4C4SbPh + 2 LiCl (Ph = C6H5) It is yellow oil that resinifies (polymerizes in an ill-defined manner) at room temperature. Antimony metallocenes are known as well:

14SbI3 + 3 (Cp*Al)4 → [Cp∗2Sb]+[AlI4]− + 8Sb + 6 AlI3 The Cp*-Sb-Cp* angle is 154°.

Reactions As soft Lewis donors, stibines form some coordination compounds.. Stibines can be oxidized with halogens:

R3Sb + Br2 → R3SbBr2 The resulting dihalides, when heated, release the organic bromide:

R3SbX2 → R2SbX + RX Up treatment with metallic sodium, one C-Sb bond breaks:

Ph3Sb + Na → Ph2SbNa + PhNa The stibine Sb(C6F5)3 is Lewis acidic. It forms an adduct with triphenylphosphine oxide, indicating a donor-acceptor interaction between the lone pair on oxygen and the σ* level assicuated with an Sb–C bond. Sb(C6H5)3 is a weaker Lewis acid than its fluorinated analogue.

Antimony(V) derivatives Major families of Sb(V) compounds are of the type SbR4+ (stibonium ions), which are tetrahedral, and pentacoordinate antimony compounds called stiboranes. Stiboranes are synthesised from stibines and halogens (Ph = C6H5):

Ph3Sb + Cl2 → Ph3SbCl2 As confirmed by X-ray crystallography, dichlorostiboranes feature pentacoordinate Sb(V) with trans-diaxial chloride ligands. The dichlorostiborane reacts with phenyl lithium to give pentaphenylantimony:

Ph3SbCl2 + 2 PhLi → Ph5Sb Pentaphenylantimony decomposes at 200 °C to triphenylstibine and biphenyl. Like the organobismuth compounds, stiboranes form onium compounds and ate complexes. Unsymmetrical stiboranes can also be obtained through the stibonium ions:

R5Sb + X2 → [R4Sb]+[X]− + RX [R4Sb]+[X]− + R'MgX → R4R'Sb In the related Me5Sb, proton NMR spectra recorded at -100 °C cannot resolve the two types of methyl protons. This observation is consistent with rapid Berry pseudorotation. Antimony resists forming multiple bonds, as anticipated by the double bond rule. Thus, it forms C6H5)3Sb(OH)2, not C6H5)3SbO. This observation contrasts with the behavior of phosphorus compounds where C6H5)3P(OH)2 is not observed and C6H5)3PO is robust. C6H5)3SbO is claimed to exist as a dimer.

Reactions Lewis acidic antimony(V) compounds have long been exploited in the form of SbF5, which forms stable conjugate non-coordinating anions (SbF−6 and Sb2F−11). Some organoSb(V) derivatives indeed are Lewis acidic.

A 9-anthracenylltriphenylstibonium cation binds fluoride to give a luminescent adduct.

Distibines and antimony(I) compounds

Distibines are formally SbII compounds, but feature tricoordinate Sb atoms with a single Sb-Sb bond. They may have interest as thermochromes. For example, tetramethyldistibine is colorless when gas, yellow when liquid, red when solid just below the melting point of 18.5 °C, shiny-blue when cooler, and again yellow at cryogenic temperatures. A typical synthesis first displaces an SbIII halide with an alkali metal and then reduces the resulting anion with ethylene dichloride. Like its lighter congener, arsenic, organoantimony compounds can be reduced to cyclic oligomers that are formally antimony(I) compounds.

Compounds with multiple bonds to Sb

Stibabenzene, a planar ring akin to benzene, can be prepared by dehydrohalogenation of an stibacyclohexadiene. Compounds have been made with the core structure C-Sb=Sb-C, the main requirement being that the organic substituent must be bulky.

Safety Antimony compounds are toxic. Organoantimony compounds occur in nature. Their biogenesis and structures are proposed to be similar to some organoarsenic derivatives.

Further reading Organoantimony-based Lewis acids C. Elschenbroich, A. Salzer Organometallics : A Concise Introduction (2nd Ed) (1992) from Wiley-VCH: Weinheim. ISBN 3-527-28165-7

References

Illustrations

Worked examples

Example 1 — a first encounter with Organoantimony chemistry

Start with the simplest possible case. Write down what Organoantimony chemistry 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 Organoantimony chemistry 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 Organoantimony chemistry 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 Organoantimony chemistry

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

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

Frequently asked questions

What is Organoantimony chemistry in simple terms?

Organoantimony chemistry is the chemistry of compounds containing a carbon to antimony (Sb) chemical bond. Relevant oxidation states are SbV and SbIII.

Why does Organoantimony chemistry 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 Organoantimony chemistry?

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 Organoantimony chemistry.