Linked Questions

2
votes
2answers
870 views

Chirality of heteroatoms [duplicate]

Why is a phosphorus atom with three different substituents chiral, but nitrogen isn't? Nitrogen inverts fast, while phosphorus obviously much slower. How is that explained?
33
votes
3answers
26k views

Why is the bond angle H-P-H smaller than H-N-H?

$\ce{N}$ & $\ce{P}$ are in the same group. Both $\ce{NH3}$ and $\ce{PH3}$ have one lone pair and according to VSEPR theory, both the central atoms are predicted to be $\ce{sp^3}$ hybridized. But ...
22
votes
3answers
6k views

Can heteroatoms with lone pairs be chiral centres?

If a compound has a carbon atom with four different groups covalently bonded to it, it is called asymmetric and enantiomers of the compound can exist. But imagine if one has a different central atom, ...
12
votes
3answers
8k views

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 ...
21
votes
1answer
2k views

What is the mathematical basis behind the Jahn-Teller effect?

Both first-order and second-order Jahn-Teller distortions play a very important role in chemistry. It is often said that the Jahn-Teller effect is based on symmetry arguments, and hence nothing can ...
20
votes
2answers
2k views

Why don't trigonal S and P compounds undergo inversion at room temperature?

Most molecules containing nitrogen atoms in trigonal pyramid configuration undergo a relatively fast process of inversion at room temperature. On the other hand, the free energy barrier for phosphines,...
16
votes
2answers
11k views

Diagonal relationships in the Periodic Table

I have often wondered about diagonal relationships between elements on the periodic table, and the most often cited explanations revolve around charge-density considerations. But other than that, ...
0
votes
1answer
2k views

Why does the PH3 geometry deviate more from the trigonal planar one, than does NH3?

$\ce{PH3}$ has a more bent structure than $\ce{NH3}$. The HOMO-LUMO gap for $\ce{PH3}$ is smaller than for $\ce{NH3}$, and so the distortion from the trigonal planar geometry is said to be larger. ...
3
votes
2answers
401 views

Why sp3 hybridisation in NH3 but bonding with pure p orbitals in case of other hydrides of group 15 [duplicate]

According to my book, the following line was given relating to the bond angle in Group 15 elements The bond angle in PH3, AsH3 and SbH3 is close to 92° which suggests that the orbitals used for ...
1
vote
1answer
402 views

How does hybridisation affect an otherwise chiral centre? [closed]

In basic theory, a carbon atom with four nonidentical substituents attached, makes a chiral centre. Thus any molecule is chiral as long as it has a chiral centre (except meso compounds). I thought ...
-2
votes
1answer
420 views

Why does NH3 hybridize at all?

So in Chemistry class I've been taught that hybridization is a way we can explain things such as how $\ce{CH4}$, for example, forms four, equally strong bonds. However at the same time I'm told that ...
1
vote
1answer
402 views

Chiral centers in albuterol-like compounds

My question is apart from the C in the straight chain with $\ce{-OH}$ group, should $\ce{N}$ be counted as chiral center since it also has tetrahedral geometry and all different substituents? There ...
2
votes
1answer
350 views

Does triphenylphosphine show resonance?

The lone pair of phosphorus and the double bonds in benzene looks to be in conjugation. Do the molecule show resonance? If so, how?