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Why is a tertiary amine with three different substituents not chiral? Doesn't the lone pair represent a fourth, different substituent?

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  • $\begingroup$ See this en.wikipedia.org/wiki/Nitrogen_inversion $\endgroup$ – Soumik Das Jun 15 '18 at 17:05
  • $\begingroup$ @SoumikDas Also addressed in this question...probably close enough to be duplicate, actually. $\endgroup$ – hBy2Py Jun 15 '18 at 17:06
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    $\begingroup$ The other question is not a fully dupe of this question... For one thing, the statement of this question is wrong. Tertiary amines can definitely be chiral. It's just that the epimerize quickly, but they are definitely chiral when there are 3 different substituents. In addition, you can easily create an tertiary amine that does not invert by tying back the substituents. $\endgroup$ – Zhe Jun 15 '18 at 17:42
  • $\begingroup$ @Zhe Sir, plz. explain a bit " you can easily create an tertiary amine that does not invert by tying back the substituents " what is"tying back the substituents" $\endgroup$ – Rafael Nadal Jun 15 '18 at 17:48
  • $\begingroup$ Constraining the substituents within a rigid structure, possibly a cyclic species $\endgroup$ – Waylander Jun 15 '18 at 18:10

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