How do electron-withdrawing groups affect basicity?

How do electron-withdrawing groups affect basicity?

You may recall that electron withdrawing atoms (e.g. F or Cl) or functional groups (e.g. NO2) tend to increase acidity, by slurping away electron density from the conjugate base. Lower charge density = more stability = lower basicity.

Does EDG increase basicity?

EDG is electron donating group and EWG/ ERG is electron withdrawing/ releasing group. And when it is increasing +I effect, then the ease of donating lone pair increases and the basicity increases and vice-versa in the case of Electron donating group (EDG).

Do electron-withdrawing groups stabilize bases?

From what I understand, EWGs stabilize acids bc they can withdraw the negative charge from the conjugate base, stabilizing the overall molecule, while EDGs stabilize bases bc they can donate electrons to the positive charge of the conjugate acid, stabilizing the overall molecule.

How does electronegativity affect basicity?

Bases donate electrons to form new covalent bonds; therefore if they have a greater attraction for electrons they are less likely to share them. As a result we see that electronegativity is related to basicity. The greater the electronegativity of an atom, the less it is willing to share its electrons.

Why does basicity decrease down a group?

Going down the group, size of the atom increases. And hence, electron density over the group 15 elements decreases. Thus tendency to donate electrons decreases and basicity decreases.

Why do alkyl groups increase basicity?

Because alkyl groups donate electrons to the more electronegative nitrogen. The inductive effect makes the electron density on the alkylamine’s nitrogen greater than the nitrogen of ammonium. Correspondingly, primary, secondary, and tertiary alkyl amines are more basic than ammonia.

How do EWG affect basicity?

Strongly electron-withdrawing groups reduce the basicity of nearby amines through the inductive effect. This reduces electron density on the amine. As the distance between the EWG and the amine increases, basicity increases.

Do electron withdrawing groups increase basicity?

The basicity of an amine is increased by electron-donating groups and decreased by electron-withdrawing groups. Aryl amines are less basic than alkyl-substituted amines because some electron density provided by the nitrogen atom is distributed throughout the aromatic ring.

How does inductive effect affect basicity?

The inductive effect also plays a vital role in deciding the acidity and basicity of a molecule. As the number of -I groups attached to a molecule increases, its acidity increases; as the number of +I groups on a molecule increases, its basicity increases.

Why does basicity decrease down the group?

Why does electronegativity decrease basicity?

However, electronegativity is the tendency for an atom to “hog” electrons. Therefore, the more electronegative, the more electrons there are in a similarly sized space. More concentrated electrons = more stable base = weaker acid.

Why does Nucleophilicity increase down the group?

A nucleophile acts by donating a pair of electrons to another atom’s nucleus. In addition, as one proceeds down a given column of the periodic table, the nucleophilicity increases because the electrons are not held as tightly to the nucleus (electronegativity decreases).

Is it possible to increase acidity with more electron withdrawing groups?

Yes and no, with more electron withdrawing groups at ortho and para positions would certainly increase acidity but other factors do play a role. For example, In trinitrobenzoic acid here the two 2 at ortho positions are very bulky and due to steric repulsion rotate the group thus making the compound non planar due…

How are electron withdrawing and donating groups related?

Ethers, -OR Alkyl groups are also weakly electron-donating. An electron withdrawing group \\, (EWG) is a group that reduces electron density in a molecule through the carbon atom it is bonded to. By reducing electron density on adjacent carbon atoms, EWGs change the reactivity of a molecule:

How are negative charges stabilized by withdrawing groups?

for a negative charge, it’s exactly the opposite. negative charges are stabilized by the presence of electron withdrawing groups, for the exact same reasons that positive charges are stabilized by electron donating groups.

How does an alkyl group reduce electron density?

Alkyl groups are also weakly electron-donating. An electron withdrawing group \\, (EWG) is a group that reduces electron density in a molecule through the carbon atom it is bonded to. By reducing electron density on adjacent carbon atoms, EWGs change the reactivity of a molecule:

https://www.youtube.com/watch?v=hZ4y5WsjdDw