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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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1 answer
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What is the three-dimensional structure of H2CSF4?

Based on Bent’s rule and hybridization, which orbitals would be used to make the π-bond between carbon and sulfur, and in which plane would each of the atoms like? To make solving the question easier (...
-2 votes
0 answers
38 views

Location of lone pair being used for back bonding, and the hybridisation of nitrogen in silyl isothiocyanate [duplicate]

The expected structure for silyl isothiocyanate is H3Si-N̈=C=S, where N has a lone pair. However, due to back bonding, the lone pair of nitrogen is shared with the d-orbital of the silicon atom. My ...
3 votes
1 answer
120 views

Why is Piperidine more basic than Pyridine? [duplicate]

Piperidine, which has sp3 carbons attached to it, experiences an increase in electron density on the nitrogen atom, making it more basic. However, when we look at the resonating structures of pyridine,...
1 vote
0 answers
46 views

Confusion in comparing contribution of resonance structures in Hydrazoic acid

Given below is the resonance hybrid of $\ce{HN3}$(Hydrazoic acid) And these are the resonance structures below: If the second resonance structure had contributed more, then the two bond lengths ...
0 votes
0 answers
57 views

Restriction of back bonding in tris(dimethylamino)borane

J.D. Lee Concise Inorganic Chemistry [3, p. 78] mentions that The bond length order of the B-N bond in the following compounds is $\ce{B(NR2)3}$ > $\ce{HB(NR2)2}$ > $\ce{H2B(NR2)}$ and the ...
-4 votes
0 answers
41 views

Effect of Vacant d-orbital of Phosphorous in Pyramidal Structure of Trisilylphosphine [duplicate]

J.D. Lee Concise Inorganic Chemistry [3, p. 77] specifically mentions that In case of $\ce{P(SiH3)3}$, the inter-nuclear distance is large and P atom has its own vacant d orbital. Hence the tendency ...
0 votes
2 answers
276 views

Do PH3F2 and XeS2 exist (in the light of hybridization and Valence Bond Theory)?

Do $\ce{PH3F2}$ and $\ce{XeS2}$ exist, in accordance with Valence Bond Theory? According to Drago's Rule, if the central atom of a compound is an element of the third period, and the attached atom has ...
66 votes
9 answers
42k views

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'...
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 $\...
0 votes
0 answers
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Why should higher energy empty orbitals be chosen over lower energy empty orbitals during hybridisation?

Organic chemistry by jonathan clayden states during his explanation of hybridisation using trigonal boron structure (sp2) and tetrahedral boron structure (sp3): You want to populate the lowest energy ...
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 ...
2 votes
0 answers
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Question Involving Bonding (VSEPR AND VBT)

So basically any chemistry book will tell you about the extent of overlapping in different orbitals. For formation of sigma bonds, head on overlapping happens. Chemistry textbooks always state that $p-...
10 votes
1 answer
412 views

What is the hybridization state of the carbon atoms in [10]annulene?

I know that one of the more stable structures of [10]annulene or cyclodecapentaene is planar boat-shaped. But that means the hybridization state of the carbons must have changed to suit the geometry. ...
2 votes
2 answers
340 views

Determining covalent bond strengths without hybridisation

Assuming pure $\ce{2s}$ and $\ce{2p}$ orbitals of carbon are used in forming $\ce{CH4}$ molecule, which of the following statements is false? (single choice question) Three $\ce{C-H}$ bonds ...
17 votes
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 ...
0 votes
0 answers
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Why is Sulfur Trioxide has SP² hybridization? [duplicate]

When I google what is the type of hybridization in SO₃ it gives me "SP² hybridization". The problem I have is why does it has the above hybridization when it has 3 double bonds with the ...
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 ...
-2 votes
1 answer
187 views

Why can s and p orbitals of one atom form hybrid orbitals but the overlaping of s & p orbitals of two different atoms don't form a molecular orbital?

So my question is in the title : Why can s and p orbitals of one atom form hybrid orbitals but the overlapping of one s orbital and one p orbital (perpendicular to the bond axis) of two different ...
0 votes
2 answers
253 views

Understanding Hybridisation in Cyclic Compounds

I had a doubt while solving this problem. At first glance of these compounds, I felt that all of them have sp3 hybridisation (for nitrogen), since all of them had 3 bonded pairs and 1 lone pair around ...
0 votes
1 answer
109 views

Do diatomic molecules undergo hybridization

For the steric number to be 1,the molecule must be diatomic or linear in geometry and shape. First of all, do they undergo hybridization? Secondly, Just like the hybridization for steric number 2 is ...
-2 votes
1 answer
145 views

Why is it okay for the central carbon to lose a bond when forming a resonance structure for acetone?

As the title reads, I'm confused as to why it's okay for the central carbon in acetone to have a +1 formal charge when we push the electrons from one of the bonds with oxygen to form a lone pair and ...
5 votes
4 answers
10k views

Is there a shortcut method to calculate the Steric Number?

The steric number is equal to the number of $\sigma$-bonds + the number of lone pairs of electrons on the central atom. It gives us the number of hybridised orbitals. It is pretty straight-forward to ...
4 votes
1 answer
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%s character distribution of phosphorus hybrid orbitals

The following question was asked in the Indian Olympiad Qualifier Chemistry Part I (IOQC) today: For the given compound, %s character of phosphorus hybrid orbitals which contribute to various bonds ...
-3 votes
2 answers
232 views

What kind of hybridisation is there around the central carbon atoms?

I am currently working on an assignment and I am confused about what kind of hybridisation exists for the first condensed structure CH3CN. Does the CH3 have sp2 hybridisation? I suspect its that ...
5 votes
1 answer
310 views

Why is pyramidal structure observed in trisilylphosphine?

Why does trisilylphosphine $\ce{P(SiH3)3}$ (ICSD Entry: 72676, [1]) have a pyramidal structure while trisilylamine $\ce{N(SiH3)3}$ (ICSD Entry: 201428, [2]) is planar? I think since silicon has a ...
6 votes
1 answer
6k views

Why are axial bonds are longer than equatorial bond in sp3d hybridized atoms?

Why are axial bonds are longer than equatorial bond in case of $\mathrm{sp^3d}$ hybridization? I have done some research but I can't seem to find the answer.
8 votes
1 answer
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Why does hybridization significantly matter for organic chemistry?

I just recalled, and still see that almost every organic chemistry book starts with bonds, empahsizing hybridization. One thing is straight forward but the rest doesn't seem to connect well. The thing ...
0 votes
1 answer
111 views

Formation of tetrafluoroborate using VBT and hybridisation

How can the formation of $\ce{BF_4^-}$(Boron is $\ce{sp^3}$ hybridized) be explained using VBT and Hybridization? So far, I understood that one electron from s orbital gets excited and jumps into a p ...
1 vote
2 answers
301 views

Molecular orbital picture in conjugated molecules - double bonds

I am a not a chemistry student but a physics student. Nevertheless, I am quite familiar with molecular orbital theory and similar quantum chemistry concepts. However, I have problems understanding the ...
0 votes
0 answers
39 views

If Ethyne has the lowest C-H bond length (highest C-H bond energy) compared to Ethane and Ethene, why is it the most acidic? [duplicate]

I am not an expert in chemistry, but these are the few facts I know from Standard XII chemistry books (these facts could be wrong or incomplete or modified by now). Facts I know - Ethane has 'sp$^3$' ...
6 votes
1 answer
4k views

What Causes Atomic Orbitals to Hybridise?

I'm finding it difficult to visualise the process of hybridisation. Taking the example of formation of $\ce{CH4}$, can it viewed as the collapsing of the p orbitals of the Carbon atoms as they get "...
-2 votes
1 answer
102 views

In which orbital is the positive charge of central nitrogen present in diazomethane? [closed]

Where is the positive charge of central nitrogen located? It cannot be in the pure p orbital because in that case there will only s-orbital left for hybridization which is not possible. If it's ...
-2 votes
1 answer
393 views

How do I determine the hybridization of terminal atoms? [duplicate]

I've read that terminal atoms do not undergo hybridization because there is no need to. For example, CF4, C undergo sp hybridization, but fluorine do not hybridize. How about CO2? Why is oxygen sp2 ...
8 votes
1 answer
6k views

Hybridization, MOT and Paramagnetism

In what way can hybridization or molecular orbital theory be used to explain paramagnetism? For instance, when something is hybridized to make enough bonding electrons, do all the electrons end up ...
5 votes
1 answer
10k views

Sulfur trioxide - vacant d-orbitals

Sulfur trioxide violates the octet rule. Upon drawing the Lewis dot structure for sulfur trioxide, we see that the central sulfur atom is bonded to three other oxygen atoms by double covalent bonds. ...
0 votes
0 answers
111 views

What is the logic behind the steric number formula?

My teacher taught us two methods two calculate steric number for determining hybridisation. The first method was to count the total number of sigma bonds and add the lone pairs of the central atom. I ...
1 vote
0 answers
45 views

Is there a molecular orbital equivalent of rehybridization?

I generally have seen the pyramidal inversion of NH3 explained in terms of rehybridization. The sp3 hybridized NH3 changes to sp2, with the lone pair in the p orbital, and then reverts to sp3 in the ...
4 votes
0 answers
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Is the shortness of boron trifluoride's bonds better understood and explained now than it was "way back" in the 20th century?

Wikipedia's Boron trifluoride; Structure and bonding says: In the boron trihalides, BX3, the length of the B–X bonds (1.30 Å) is shorter than would be expected for single bonds,7 and this shortness ...
9 votes
2 answers
636 views

Bonding in hypervalent molecules

I don't know where they go the electrons of the extended-valence in molecules like $\ce{SF6}$ or $\ce{PCl5}$ for instance because my teacher said that the d orbitals can't interact with s and p (or ...
2 votes
1 answer
1k views

Why is the bond angle of SO2 less than 120 degrees? [duplicate]

I've learnt about VSEPR theory and have a general idea of how lone electron pairs affect the molecular geometry by repulsions. But my teacher told me that when the angle between bond pairs or lone ...
0 votes
0 answers
63 views

What does "shape of hybrid orbitals" mean?

My teacher and textbook distinguish between the $sp$,$sp^2$ and $sp^3$ hybrid orbitals' shapes by saying that the first has linear shape, the second has trigonal shape, and the third has tetrahedral ...
1 vote
2 answers
376 views

Why are there FOUR $sp^3$ hybridized orbitals in methane?

(This may be a stupid question, but I've only learnt about hybridization yesterday.) I will take the example of methane. The valence shell electron configuration of ground state of carbon is $2s^2 2p^...
0 votes
2 answers
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How to predict molecular geometry of acetylene using VSEPR model?

I need to determine the molecular geometry of acetylene. For this I performed the following procedure. First, I drew the correct Lewis structure which is a graphical representation that shows the ...
1 vote
0 answers
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Is it possible to have different isomers of compounds with SP2 hybridized carbons based on the orientation of the Pi bond?

I was building molecular models with my son who is in high school to teach him about molecular geometries and he asked me a question I had never considered before. We built Acetone, using plastic ...
0 votes
2 answers
770 views

Is fluorine also hybridised in carbon tetrafluoride?

I had read that when an atom forms multiple bonds, it hybridises it's orbitals to minimise the repulsion and decrease the overall energy. But do the terminal atoms also exist in hybridised form? E.g. ...
-1 votes
1 answer
787 views

What is the hybridization of oxygen atoms in boric acid?

I was making the $\ce{H3BO3}$ structure and tried to think of hybridization of oxygen atoms and got confused between $\mathrm{sp^2}$ and $\mathrm{sp^3}$. Boron has empty orbitals, so the lone pairs of ...
-4 votes
1 answer
352 views

Why is hybridization different in a ring? [duplicate]

Why is nitrogen $sp^3$ hybridized in a compound such as NH3 but $sp^2$ hybridized in something like pyrrole, which has a ring structure? In both cases there are three bonds and one lone pair.
12 votes
2 answers
2k views

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 ?
3 votes
2 answers
3k views

Why is sulfur unhybridized in dimethyl sulfide?

In which of the following molecules is the central atom unhybridized: (a) $\ce{S(CH3)2}$ (b) $\ce{SO2}$ (c) $\ce{SiH4}$ (b) $\ce{PCl3}$ The answer given is (a), but I can't figure out ...
7 votes
1 answer
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Why do sp³ orbitals have tetrahedral symmetry when they are linear combinations of orbitals with octahedral symmetry?

I'm trying to understand how orbitals hybridize. What I understand—or at least think I understand—is the following: The "standard" $\mathrm{s}, \mathrm{p}, \mathrm{d}, …$ orbitals are ...

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