redfox Posted March 13, 2008 Share Posted March 13, 2008 I'm sure this is simple enough but for some reason my brain is not willing to work with me! Theobromine (a structural analogue of caffeine) dissolves easily in acids and bases, but is poorly soluble in water. Why is that?? Thanks for any advice offered:) Link to comment Share on other sites More sharing options...
thedarkshade Posted March 13, 2008 Share Posted March 13, 2008 Ah, the 'food of gods'! I don't really know the answer, but probably because water is incapable of breaking the bonds that exist between the atoms of theobromine. Just a guess! BTW, Wiki says theobromine is water insoluble Link to comment Share on other sites More sharing options...
redfox Posted March 14, 2008 Author Share Posted March 14, 2008 Erm, first of all NEVER use wikipedia, it's a pile of poo! And monkeys probably write half the stuff on there;) Second, it is classed as poorly water soluble, this is because it takes around 2000ml of water to dissolve 1g of Theobromine. It's called water-insoluble 'cos that's far above the amount it would require if it were water-soluble, however it's not technically 'insoluble'. Thanks for the response tho, I reckon it is something to do with pH... Link to comment Share on other sites More sharing options...
John Cuthber Posted March 16, 2008 Share Posted March 16, 2008 My best guess is that it forms salts with acids and bases. The salts are more polar than the original molecule and are more water soluble. BTW, if you think Wiki's wrong then why not correct it? Link to comment Share on other sites More sharing options...
YT2095 Posted March 16, 2008 Share Posted March 16, 2008 Solubility: Very slightly soluble in cold water. taken from: http://64.233.183.104/search?q=cache:4gsYRaViqgcJ:www.sciencelab.com/xMSDS-Theobromine-9925229+Theobromine+MSDS&hl=en&ct=clnk&cd=1&gl=uk&client=firefox-a just look up the MSDS for it. Link to comment Share on other sites More sharing options...
John Cuthber Posted March 16, 2008 Share Posted March 16, 2008 I don't think the original question is about the exact solubility, but about why it dissolves much better in acids or bases than in neutral conditions. Link to comment Share on other sites More sharing options...
redfox Posted April 3, 2008 Author Share Posted April 3, 2008 BTW, if you think Wiki's wrong then why not correct it? Hah, I would but I don't know all the details of everything yet;) It's ok as a starting point, but should never be used for reference. It's not that I think it's rubbish in every aspect, but considering I could just go in there and change it with no knowledge on a subject...I think that says a lot about it's reliability:) Anyway, thanks for advice everyone. Yes the question was about why it dissolves in acid and bases and not water. I think acids, bases and pH7 of water is a hint. Maybe it's because it's zwitterionic and needs a definite electron acceptor/donator. I think. The structure must have something to do with it, but I'm not entirely sure what... Link to comment Share on other sites More sharing options...
ChemCed Posted August 22, 2008 Share Posted August 22, 2008 Theobromine means.... Theo(God) + Bromine.... hahahahahaha! Link to comment Share on other sites More sharing options...
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