chirality of nitrogen

[podyon18]

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Is a nitrogen compound with 3 different substituents and a lone pair chiral?

thanks!!

 

[Dasypus]

Not usually, but you're right that it's not straightforward. The lone pair can usually flip back and forth between the other three substituents, like turning a sock inside out. Sometimes though, if a molecule is rigid enough, this isn't possible, and it can form a chiral center. I'm willing to bet we won't be asked about something like that, but you never know.

http://en.wikipedia.org/wiki/Nitrogen_inversion

 

[gettheleadout]

Dasypus is right, nitrogen is essentially never chiral because the lone pair exists in an extremely fast equilibrium between the two possible positions.