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Inorganic reaction mechanism query

  • 24-03-2010 10:55am
    #1
    Closed Accounts Posts: 5


    Hello, I'm hoping someone can help me shed some light on this. I've come across a reaction in a book that's relevant to the research I'm doing. However, I can't seem to fully figure out how the reaction proceeds from start to finish (my background is not in chemistry). If I could see one or two intermediate reaction mechanisms with curly arrows it might clear things up for me. Does anyone have any suggestions for one or two intermediate reaction mechanisms? I know the presence of copper plays an important role and that the amide nitrogen now plays an important part in the bonding with new reaction centres becoming involved in the bonding of the peptide after the ionisation of the amide proton. Any atom with lone pairs can coordinate to the copper cation. The more basic, the more likely it will coordinate. When you deprotonate the nitrogen, it is more nucleophilic and basic than the carbonyl oxygen, so the result is that the two point binding of this molecule changes.After that I'm lost - can't figure out how to draw the intermediate diagrams. Any help would be greatfully appreciated. I've attached the start and end diagrams (hopefully!)


Comments

  • Registered Users, Registered Users 2 Posts: 22 hairyeggs


    The first compound does not look right - you have 3 covalent bonds to a neutral oxygen.


  • Closed Accounts Posts: 5 Chembelle


    I've attached all the information I have so far. I just need to figure out the intermediate structures (provided the initial ones are correct!). I think the effect of the Cu ion enables the unusual binding. Any help would be much appreciated.


  • Registered Users, Registered Users 2 Posts: 22 hairyeggs


    What is the original source? Both of first two figures also contain mistakes - missing charges on the oxyanions.


  • Closed Accounts Posts: 5 Chembelle


    The original source is a section of a book. Essays in Chemistry (1977), 6, 1, 33. J.N. Bradley, R.D. Gillard and R.F. Hudson (Ed). I found it online as an excerpt but the diagrams weren't very clear, the negative charge on the oxyanion in the first diagram should be there but it may not have scanned well or something.
    I was hoping to reference it for a report I'm writing as I thought it had some good information in it that was relevant to the work I'm doing. Thanks for taking the time to look through this, I'm very grateful.


  • Registered Users, Registered Users 2 Posts: 22 hairyeggs


    Could you post a scan of the relevant page from the original book?


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  • Closed Accounts Posts: 5 Chembelle


    I've spent the last few days trying to obtain the original source to no avail. The online link has also been removed - I think it was from a lecture.


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