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Questions tagged [hybridization]

Hybridisation is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties.

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What is Bent's rule?

I'm all bent out of shape trying to figure out what Bent's rule means. I have several formulations of it, and the most common formulation is also the hardest to understand. Atomic s character ...
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Why is it wrong to use the concept of hybridization for transition metal complexes?

I have asked a lot of questions on coordination chemistry here before and I have gone through a lot others here as well. Students, including me, attempt to answer those questions using the concept of ...
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Why does F replace the axial bond in PCl5?

Why does $\ce{F}$ replace an axial bond in $\ce{PCl5}$? I realize that it would be more stable there than at equatorial bond, but what is the reason of its stability? Similarly in $\ce{AB4}$ type of ...
Shubham's user avatar
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9 answers
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Why do compounds like SF6 and SF4 exist but SH6 and SH4 don't?

Both $\ce{SF6}$ and $\ce{SH6}$ and $\ce{SF4}$ and $\ce{SH4}$ have the same central atom and the same hybridization, but my teacher specifically mentioned that $\ce{SH6}$ and $\ce{SH4}$ don't exist. I'...
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55 votes
4 answers
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How do I figure out the hybridization of a particular atom in a molecule?

I'm learning how to apply the VSEPR theory to Lewis structures and in my homework, I'm being asked to provide the hybridization of the central atom in each Lewis structure I've drawn. I've drawn out ...
Melanie Shebel's user avatar
53 votes
3 answers
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What makes banana bonds possible in diborane?

Diborane has the interesting property of having two 3-centered bonds that are each held together by only 2 electrons (see the diagram below, from Wikipedia). These are known as "banana bonds." I'm ...
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Why does bond angle decrease in the order H2O, H2S, H2Se?

I know that bond angle decreases in the order $\ce{H2O}$, $\ce{H2S}$ and $\ce{H2Se}$. I wish to know the reason for this. I think this is because of the lone pair repulsion but how?
Yomal Amarathunge's user avatar
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Are the lone pairs in water equivalent?

I've read that the oxygen atom in water is $\mathrm{sp^2}$ hybridized, such that one of the oxygen lone pairs should be in an $\mathrm{sp^2}$ orbital and the other should be in a pure p atomic orbital....
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44 votes
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Carbon atoms at the edge of a diamond

It is well known (the simplest textbook example) that a diamond has a well-defined arrangement of sp3 carbon atoms, as each atom is connected to four others in a ...
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What is Drago's rule? Does it really exist?

My textbooks states the Drago's rule in inorganic chemistry as follows: The more electronegative atom prefers the orbital having more $\mathrm{p}$ character, and lone-pairs or less electronegative ...
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Sp5 hybridization in cyclopropane?

I have never before heard/read about something as a $sp^5$ hybridization. Today, Henry Rzepa's blog post made me aware of the existance of such a bonding system. That made me search a little bit and I ...
pH13 - Yet another Philipp's user avatar
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Are the bonding orbitals in methane equivalent - photoelectron spectrum

The low energy portion (the part dealing with the $\ce{2s}$ and $\ce{2p}$ electrons) of the photoelectron (PE) spectrum of methane is reproduced below. (image source) The reaction being examined is ...
ron's user avatar
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d-orbital splittings in WS2 monolayer

The formerly degenerate $d$ orbitals of the tungsten atoms in the $\ce{WS2}$ monolayer are split into three groups: (1) $\mathrm{d}_{z^2}$, (2) $\mathrm{d}_{x^2-y^2}, \mathrm{d}_{xy}$ and (3) $\mathrm{...
Capo Mestre's user avatar
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How to rationalise the resonance structures and hybridisation of the nitrogen in a conjugated amine?

I was given the first structure, and then drew the other 5 resonance structures: First of all, are they correct? ChemBioDraw had some complaints, but as far as I can see there's the same number of ...
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27 votes
2 answers
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Is hybridization used in ab initio valence bond calculation?

Many general chemistry textbooks introduced the concept "hybridization" to construct a symmetry-adapted VB-type wavefunction. In the textbooks, usually the minimal basis is used and without optimizing ...
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Why can there not be more than one sigma bond in a set of bonds?

A question on an exam asked why there is exactly one sigma bond in double and triple covalent bonds. I looked in my text and online after the exam, but couldn't find an anawer to the question. Why ...
Hal's user avatar
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Does nitrogen inversion affect the basicity of amines?

If I were to compare the basic strength of 1-azabicyclo[2.2.1]heptane and triethylamine: Can I say that 1-azabicyclo[2.2.1]heptane is more basic than triethylamine because the lone pair of electrons ...
Aditya Dev's user avatar
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What is the origin of the differences between the MO schemes of O₂ and N₂?

Here are the MO schemes of $\ce{N2}$ (left) and $\ce{O2}$ (right). Why is the $\sigma$-MO formed by the $p$ AOs energetically above the $\pi$-MO for $\ce{N2}$ but not for $\ce{O2}$? Can it be ...
EJC's user avatar
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How can the Bonding in IF7 be explained using LCAO method?

I know that the VSEPR theory explains $\ce{IF_7}$ (iodine heptafluoride)'s structure as a pentagonal bi-pyramidal one. The valence bond theory can be used to say that it has $\mathrm{sp^3d^3}$ ...
scienceauror's user avatar
22 votes
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What is natural bond orbital theory used for?

My understanding is that the NBO methodology transforms the molecular orbital picture of a molecule into a collection of pairwise interactions (bond orbitals). This is obviously handy for didactic and ...
Richard Terrett's user avatar
22 votes
3 answers
1k views

Non-integer hybridization

I've known that hybridization in distorted geometries is not exactly $sp^3$ or $sp^2$ or whatever. For example, $\ce{PH3}$ has nearly pure $p$ orbitals in the $\ce{P-H}$ bond, and the lone pair is in ...
ManishEarth's user avatar
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Relative acidities of alkanes, alkenes, and alkynes

How does one explain the trend in bond lengths and acidity of the following hydrocarbons? $$\begin{array}{ccc} \hline \text{Species} & \ce{C-H}\text{ bond length / Å} & \mathrm{p}K_\mathrm{a} ...
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What does it mean when it is said that an sp³ orbital has 25% s character?

My textbook frequently mentions: $\mathrm{sp^3}$ hybrid orbital has 25% $\mathrm{s}$-character and 75% $\mathrm{p}$-character. What are these "characters"? And how do these characters influence ...
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19 votes
3 answers
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Why is one lobe of an sp3 hybridized orbital smaller than its other half?

A hybrid sp3 orbital is drawn with one lobe smaller than its other half, the latter which is of equal size when drawing the p orbital. Why is it so?
Apoorv's user avatar
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What is the hybridization of the carbonyl oxygen in a carboxylic acid?

My professor sent out a review guide. One of the questions on this guide is The carboxylic acid carbonyl oxygen is: 1. $\ce{sp^2}$ 2. $\ce{sp^3}$ 3. $\ce{H}$-bond donor 4. rapidly ...
user15750's user avatar
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18 votes
3 answers
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Hybridisation of Mn in potassium permanganate

I'm clear with the concepts of crystal field theory. But I can't figure out the exact reason why the hybridisation of manganese in potassium permanganate ($\ce{KMnO4}$) is $\mathrm{d^3s}$. Can anyone ...
Devgeet Patel's user avatar
18 votes
2 answers
4k views

Color of chromate and permanganate

I've heard quite a few times that the chromate and permanganate have a $d^3s$ configuration. Also, their colors arise due to a rapid switching of electrons between the oxygen and metal atoms. I don't ...
ManishEarth's user avatar
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How does VB theory explain the Si-O-Si bond angles in SiO2?

Silicon dioxide has a huge variety of structures. Most of them are built up from connected $\ce{SiO4}$ units — the $\ce{O–Si–O}$ angle is $109.5°$, accordingly. The VB/hybridization approach to this ...
Corundum's user avatar
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4 answers
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Hybridization of nitrogen in trisilylamine, (SiH3)3N?

I want to know the hybridization of the central atom in $\ce{(SiH3)3N}$. I think it should be $\mathrm{sp^3}$, because $\ce{N}$ is attached to three silicon atoms and one lone pair. But actually it ...
hey's user avatar
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17 votes
2 answers
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Predicting sigma bond overlap strengths of s-s, p-p, s-p, sp-sp etc

How can we qualitatively predict $\sigma-$bond strengths of overlap between: $\ce{s-s}$ $\ce{s-p}$ $\ce{p-p}$ $\ce{sp-s}$ $\ce{sp-p}$ $\ce{sp-sp}$ etc.? My school-book says $\ce{s-s}$ overlap bond ...
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2 answers
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What utility does the tau bond model of orbital overlap have?

In his book on molecular orbital theory, Molecular Orbitals and Organic Chemical Reactions, Ian Fleming notes that Pauling formulated an early alternative model to Hückel theory for explaining the ...
Greg E.'s user avatar
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15 votes
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Is s-p mixing referring to hybridization or is it the mixing of one atoms s orbital with the other's p orbital?

According to molecular orbital theory s and p orbitals can mix if they are close enough in energy to each other. For period 2 diatomics, this occurs for $\ce{Li}$, $\ce{Be}$, $\ce{B}$, $\ce{C}$ and $\...
RobChem's user avatar
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14 votes
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Hybridization of sulfur in sulfur dioxide

One of the canonical structures for sulfur dioxide - $\ce{SO2}$ - has sulfur (with a lone electron pair) double bonded to each oxygen atom to form a total of 4 bonds for sulfur - which can be achieved ...
Mark Adams's user avatar
14 votes
1 answer
27k views

How to rationalise the planar structre of I2Cl6?

$\ce{I2Cl6}$ is a dimer of $\ce{ICl3}$. $\ce{ICl3}$ is T-shaped, with $\ce{I}$ being $\mathrm{sp^3d}$ and having two lone pairs. I read in Inorganic Reaction Mechanisms by R. K. Sharma that $\ce{I2Cl6}...
Shodai's user avatar
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1 answer
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What is the hybridisation of trifluoromethyl free radical?

Having three σ bonds in a similar manner to $\ce{CH3^·}$ free radical, $\ce{CF3^·}$ should also have $\mathrm{sp^2}$ hybridisation. However, if we look at its shape, it is pyramidal and not planar ...
James Hunt's user avatar
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1 answer
2k views

Bonding in Square Antiprismatic Compounds

Both $\ce{IF_8^-}$ and $\ce{XeF_8^{2-}}$ have (distorted) square antiprismatic geometries. I've been wondering how to explain the bonding in such compounds. Hypercoordinate bonding (as used to ...
ron's user avatar
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14 votes
2 answers
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How to find if the unpaired electron is placed in hybrid orbital or pure orbital in odd electron species?

Odd electron species contain an unpaired electron which can either be placed in hybrid orbital or in pure orbital. Example: In the case of $\ce{.CF3}$ radical, the unpaired electron is placed in $\...
Arishta's user avatar
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13 votes
3 answers
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Do filled Orbitals also hybridize?

Recently I was watching a video on Valence Bond Theory, on the MIT Open-Course youtube channel. The teacher there said that For hybridization to occur, electron promotion from fully filled ...
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13 votes
2 answers
16k views

Are carbocations necessarily sp2 hybridized and trigonal planar?

My copy of Pearson's Organic Chemistry (7e), Morrison and Boyd, under the section "Reaction intermediates", accords a succinct description on the structure of carbocations: The central $C$-atom (of ...
paracetamol's user avatar
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Does sulfur and phosphorus expand their octet?

There are many compounds in which the stability of a molecule is not governed by the presence of octet configuration in central atom. In most of the cases the central atom is generally sulfur or ...
agha rehan abbas's user avatar
13 votes
2 answers
8k views

How do I compare the C=C bond lengths in this cumulene?

How do I arrange these chemical bonds in an increasing/decreasing order based upon their lengths? I understand that the bond (a) will be longer than (b) because (a) is a bond between sp² hybrid and ...
ExistentialNihilist's user avatar
13 votes
2 answers
31k views

Why is the lone pair of pyridine's nitrogen atom not part of the aromatic ring?

In pyrrole, the lone pair of electrons belonging to the nitrogen is part of the aromatic ring. However, in pyridine it is part of an sp2-hybridized orbital. Why can't it be in the p-orbital and take ...
CowperKettle's user avatar
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12 votes
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Does s stand for sigma bond and p for pi bond?

When we are talking about hybridization, in $\mathrm{sp/sp^2/sp^3}$ hybridization, does s stand for sigma bond and p for pi bond ?
Vedant's user avatar
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Is nitrogen of aniline sp² or sp³ hybridized? [duplicate]

I found a thread which discussed this which totally confused me. (refer to the part of the link which talks about $\ce{sp^2/sp^3}$) The question "How to rationalise the resonance structures and ...
Wong's user avatar
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Why are sp hybridized carbocations high energy?

You don’t see carbocations on double bonds very much, and here's a good reason: compared to sp3, there is more s character in the orbitals, so the empty orbital is held more closely to the nucleus. ...
Dissenter's user avatar
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1 answer
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Structure of Benzyne [duplicate]

I have seen in a lot of pictures that benzyne looks like: But aren't $\ce{C_6}$ and $\ce{C_5}$ $-$ $\ce{sp}$ hybridized? And hence bond angle should be $180^{\circ}$ or at least near about it? ...
NeilRoy's user avatar
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11 votes
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Hybridisation of ClO2

Find the hybridization as well identify the pπ-pπ as well as pπ-dπ bonds in $\ce{ClO2}$. $\ce{ClO2}$ has 2 $\sigma$ bonds, 1 lone pair, 2π bonds and 1 odd electron. Hybridisation is equal to number ...
Abhinav's user avatar
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2 answers
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What is the hybridization of the nitrogen in the azide ion?

In the azide ion, there is a symmetrical arrangement of three nitrogen atoms. If I've been told to figure out the hybridization of each nitrogen atom, what's the best way to go about doing this? My ...
Ben Tollen's user avatar
11 votes
2 answers
8k views

Is the phenyl cation or ethynylium more stable?

I recently gave an exam and I received an interesting question to which I believe the answer is wrong. Given two compounds, a benzene molecule with carbocation at one of its constituting carbon atoms ...
Abhinav's user avatar
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1 answer
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When is there hybridization and when is there no hybridization?

When is there hybridization and when is there no hybridization? Do all structures have hybridization or only some specific structures have it and why?
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