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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Leonidfly on August 17, 2011, 01:50:10 AM

Title: please help: tautomerism
Post by: Leonidfly on August 17, 2011, 01:50:10 AM

I Would like to ask anyone can help me to figure out if this molecule- "mycosporine-glycine" can have tautomer

Title: Re: please help: tautomerism
Post by: sjb on August 17, 2011, 02:25:21 AM

Quote from: Leonidfly on August 17, 2011, 01:50:10 AM

I Would like to ask anyone can help me to figure out if this molecule- "mycosporine-glycine" can have tautomer

What structural features do you know that may lead to the existence of tautomers?

Title: Re: please help: tautomerism
Post by: Leonidfly on August 17, 2011, 10:02:01 PM

keto-enol tautomers, but I don't how and where proton transfer. I'm not chemist at all.

Title: Re: please help: tautomerism
Post by: fledarmus on August 18, 2011, 05:14:30 PM

Are you referring to this compound?

http://en.wikipedia.org/wiki/File:Mycosporine-2-glycine.svg (http://en.wikipedia.org/wiki/File:Mycosporine-2-glycine.svg)

If so, the tautomer would be formed by protonating the upper nitrogen, deprotonating the lower nitrogen, and moving the double bonds appropriately.