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What is the basicity of carbon: primary, secondary, tertiary

  1. Dec 12, 2016 #1
    • Please post this type of questions in HW section using the template and showing your work.
    what is the basicity of carbon: primary, secondary, tertiary, e.g. in 1-adamantylamine (C connected with N is connected also with 3 other C, 2-adamantylamine (with two other C), 1-adamantymmethylamine (with just one next carbon)? more carbons connected to this first carbon: ...-C-NH2 makes it less basic, or more?
  2. jcsd
  3. Dec 13, 2016 #2


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    You could justify putting this in the chemistry rather than the homework section. I would expect the same factors as those which make dimethylamine a stronger base (in water) than trimethylamine (pK by about one pH unit) to apply. Only it seems to me they should apply in a purer form than in those floppier molecules, so the example is quite interesting. Ought rightly to be in the textbooks ahead of those examples.

    What the pK's actually are I don't know. Sure they must both have been measured. I soon found but couldn't see because behind a pay wall a very complete study of the 1- compound http://pubs.acs.org/doi/pdf/10.1021/je00033a015, didn't find the 2-

    Tell us if you find any answers.
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