Why do these Nitrogens experience steric hindrance?

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In summary, the steric hindrance caused by the bulky methyl groups bonded to each nitrogen in this compound makes it a weak nucleophile. The location of the nitrogens on the ring also contributes to this steric effect. However, despite this hindrance, the compound is a strong base due to the ability of protons to access the lone electron pair on the nitrogen. This makes it a useful non-nucleophilic base, along with other examples such as LDA and LHDMS, for avoiding unwanted nucleophilic side reactions.
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Wikipedia says that the steric hindrance makes this a weak nucleophile, but what exactly is it about the N's that is sterically hindered?
I realize that the N's are bonded covalently 3 times so each N has a lone pair e-, but is it the location on the ring that makes for steric effects for this molecule? thanks for any help
 
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The nitrogens are tertiary amines: the methyl groups bonded to each of the nitrogens take up a lot of volume around the nitrogens' lone pairs. This makes it very difficult for the lone pairs to participate in a nucleophilic addition or substitution: there's just not much room for a decent-sized molecule to hang onto one of those tertiary amines. However, this compound is a very strong base (this particular compound is known as "proton sponge"). It's a member of a class of compounds known as non-nucleophilic bases. Other examples include LDA and LHDMS. The main feature is a tertiary amine nitrogen with bulky (sterically hindering) electron donating groups. The idea is that steric hindrance prevents the amine from adding in a nucleophilic addition or substitution, but a proton is small enough to access the lone electron pair on nitrogen. This means you can use these compounds as strong bases and not have to worry about them participating in unwanted nucleophilic side reactions.
 
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FAQ: Why do these Nitrogens experience steric hindrance?

1. Why do nitrogen atoms experience steric hindrance?

Nitrogen atoms experience steric hindrance because they have a relatively large size and a high electronegativity, which causes them to repel other atoms or groups that are nearby.

2. What is the effect of steric hindrance on nitrogen-containing molecules?

The effect of steric hindrance on nitrogen-containing molecules is that it can limit the rotation of bonds and restrict the molecule's overall shape and flexibility. This can affect the molecule's reactivity and stability.

3. How does the steric hindrance of nitrogen atoms impact chemical reactions?

The steric hindrance of nitrogen atoms can impact chemical reactions by affecting the accessibility of the nitrogen atom for reactants or reagents. It can also affect the orientation of the reactants and the stability of the transition state, potentially slowing down or preventing the reaction from occurring.

4. Can steric hindrance of nitrogen atoms be predicted or controlled?

Steric hindrance of nitrogen atoms can be predicted and controlled to some extent. The size and shape of the substituents attached to the nitrogen atom can be adjusted to minimize steric hindrance and improve the molecule's reactivity and selectivity in reactions.

5. Are there any exceptions to the steric hindrance of nitrogen atoms?

There are some exceptions to the steric hindrance of nitrogen atoms, such as in certain bulky substituents where the steric hindrance may be minimized due to the specific conformation of the molecule. Additionally, the presence of other functional groups or solvent effects can also influence the steric hindrance experienced by nitrogen atoms in a molecule.

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