35k views

### 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 ...
8k views

### Is buckminsterfullerene aromatic?

According to Wikipedia, The $\ce{C60}$ molecule is extremely stable,[26] withstanding high temperatures and high pressures. The exposed surface of the structure can selectively react with other ...
6k views

### Is the S–O bond strength in sulfur trioxide or sulfite anion larger?

Can you please explain the difference between the bond enthalpies in sulfurtrioxide $\ce{SO3}$ and the sulfite anion $\ce{SO3^{2-}}$?
29k views

### Why is the bond order in the SO₃ molecule 1.33 and not 2?

$\ce{SO3}$ molecule has three double bonded oxygen to the central sulfur atom. Sulfur has $\ce{sp^2}$ hybridization and it has 6 outer electrons which make the bonds with the oxygen. So shouldn't ...
5k views

### Utility of Bent's Rule - What can Bent's rule explain that other qualitative considerations cannot?

Does Bent's rule have any utility? I got a vehement earful for "NO." Points raised by my professor: Coulombic considerations can be used to rationalize bond angles, strengths, and lengths without ...
9k views

### Delocalization of π-electrons in nitrate ion

Benzene and nitrate ion are given in my textbook as examples for the delocalization of π-electrons. Benzene, due to symmetry of its resonating structures, is simple enough. We assume that σ-electrons ...
1k views

### Can a cyclic amine form an amide?

This is a question from the Cambridge International Examinations October/November 2017 (pdf from papers.gceguide.com, pdf via the Wayback Machine). I need to understand why the secondary amine in the ...
12k views

### Backbonding in molecules like BF3

Can anyone please briefly explain to me the concept of backbonding along with necessary conditions for backbonding with some example? As I understand, backbonding is a donation of electron from ...
6k views

### Why isn't the side chain of arginine totally protonated at low pH?

I was wondering why arginine cannot be protonated at $\mathrm{pH\ 0}$ on all the $\ce{N}$ atoms in the side chain, as they all have a free electron pair. As this image shows, it can only be protonated ...
2k views

### Why are tertiary carbocations so stable?

Today our lecturer provided this data to illustrate the relative stability of carbocations. \begin{array}{|c|c|c|c|c|} \hline \text{Substrate} & \ce{t-BuBr} & \ce{i-PrBr} & \ce{EtBr} &...
962 views

### What is three dimensional aromaticity?

I have recently come across a statement which states: The relative stability of the 1,3-dehydro-5,7-adamantanediyl dication is ascribed to its three-dimensional aromaticity. [1] My ...
While going through a textbook, I came across the following line: $\ce{R3C-}$ is pyramidal while $\ce{(CN)3C-}$ is planar due to lack of back bonding from the lone pair of carbon atom into the \$\pi^...