I want to use a compound that will only react with amine groups even if the reaction is carried out in the presence of hydroxyl or carboxyl groups.
Typically, an amine is much more nucleophilic than a hydroxy or a carboxylic acid. So a range of protecting groups might work (Boc, Fmoc, silylgroups if you want it quite labile). An exception can be if it's an aromatic amine, because they are much less nuleophilic due to the lone pair of the amine being in conjugation with the aromatic ring. The best source for info about protection groups is the Greene Wuts : http://onlinelibrary.wiley.com/book/10.1002/0470053488
Best of luck, Anne
As you know, ketones do not usually react with –OH or -COOH groups under normal conditions, so in the following 2 examples you can just have reactions directed to the amines specifically: i) Ketones (e.g. acetone) react with primary amines (e.g. ethylamine) to give a reaction product (a carbinolamine) that dehydrates to yield ketimines (Schiff bases).
2) Also, If you react secondary amines (e.g. dimethylamine) with ketones (e.g. cyclohexanone), enamines form.
Thank you Dr. Staubitz and Dr. Matar. Both answers are helpful. I'm trying to quantify amine groups and hydroxyl groups created on multi walled carbon nanotubes because i suspect that the process I'm using might be creating both.
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