Tuesday 3 July 2007

Quinine (for real)

I wrote about quinine a while ago. I was told that I had the structure wrong. This is what it should look like.

The difference is the configuration at the stereogenic quinuclidine carbon.

An important difference to the "epi-quinidine" which I drew before is that a hydrogen bond is not possible. In the picture below it can be seen that the -OH and N are bent away from each other.

Rotation around the σ-bond that would lead to an H-bond is not possible for steric reasons.

This is apparent in the spacefill model.

I used the typical programs (I wrote about before) and the Open Babel package that I recently read about at Noel's blog. It's a convient way for converting chemical file types. It was very useful for passing structures between the different modelling and graphics programs.

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