nbritton Posted January 11, 2014 Share Posted January 11, 2014 (edited) Hi, Does anyone know what lithium precursor is strong enough to pop off the hydrogens from di-hydro lipoic acid (DHLA)? Lipoic acid is normally a disulfide bond, DHLA is the reduced form with the disulfide bond cleaved to produce two free thiol groups. The following is the structure of the compound I would like to make, it's simply DHLA with the hydrogen bonds replaced with lithium: C(CCC(=O)[O-].[Li+])CC(CC[s-])[s-].[Li+].[Li+] I tried lithium hydroxide and a white precipitate formed. However, I think this was merely lithium carbonate: 2LiOH + CO2 -> Li2CO3 + H2O. For both of the thiols in DHLA, they reportedly have a pKa of 10.7 (25C). Thanks. Anyone want to take a stab at this one?: C(CCC(=O)[O-].[Li+])CC(CC[s-])[s-].[Mg++] Edited January 11, 2014 by nbritton Link to comment Share on other sites More sharing options...
nbritton Posted January 11, 2014 Author Share Posted January 11, 2014 What would the pH be if you added 4 grams of elemental lithium to 600 mL of distilled water? With a pKa of 10.7, it appears I may not have had enough lithium hydroxide to deprotonate the thiol groups. I suppose the more relevant question is how much lithium hydroxide do I need to deprotonate, 1 gram, dihydro-lipoic acid in a solution of, 100 mL, distilled water? Link to comment Share on other sites More sharing options...
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