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Although the inversion barrier for trimethylamine is only 6 kcal/mole, that for

ID: 799488 • Letter: A

Question


Although the inversion barrier for trimethylamine is only 6 kcal/mole, that for the heterocyclic tertiary amine N-methylaziridine is about 19 kcal/mole.  Propose an explanation; you are encouraged to draw structures.  Give a brief explanation using one regular length sentence.

Although the inversion barrier for trimethylamine is only 6 kcal/mole, that for the heterocyclic tertiary amine N-methylaziridine is about 19 kcal/mole. Propose an explanation; you are encouraged to draw structures. Give a brief explanation using one regular length sentence.

Explanation / Answer

A Banana bond is formed in N-methylaziridine. Which is a general representation of electron density or configuration resembling a similar "bent" structure within small ring molecules. This bond requires high amount of energy to break.
The bond angles in aziridine are approximately 60