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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: anupree86 on August 04, 2015, 12:54:17 AM

Title: Amides decompsoition on silica
Post by: anupree86 on August 04, 2015, 12:54:17 AM

My question is whether amides decomposes on silica? Because I have tried to purify my compound containing amide linkage on silica column but I feel it decomposed on column.

Thanks,
Anuradha

Title: Re: Amides decompsoition on silica
Post by: discodermolide on August 04, 2015, 01:47:18 AM

I suppose it depends upon the amide, but it is unusual.
You feel it did!
What did you isolate?
What does it look like on TLC?

Title: Re: Amides decompsoition on silica
Post by: Dan on August 04, 2015, 03:28:29 AM

2D TLC is a good way to quickly determine whether or not your compound is unstable on silica.

There is an explanation about half way down this page (http://www.chemistryviews.org/details/education/2345141/tips_and_tricks_for_the_lab_column_troubleshooting_and_alternatives.html).

Generally, amides are stable on silica, though I have occasionally had streaking issues with them. I have the same question as discodermolide: what does it look like on TLC? Also, is the compound highly crystalline?