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

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SUMMARY

The discussion centers on the basicity of carbon in primary, secondary, and tertiary amines, specifically in the context of 1-adamantylamine, 2-adamantylamine, and 1-adamantymmethylamine. It is established that the basicity decreases as more carbon atoms are connected to the nitrogen atom, with 1-adamantylamine being more basic than its counterparts due to steric hindrance. The comparison to dimethylamine and trimethylamine illustrates that structural factors significantly influence basicity, with pKa values being crucial for understanding these differences. A complete study on the basicity of these compounds is referenced but is inaccessible due to paywall restrictions.

PREREQUISITES
  • Understanding of amine structures and classifications (primary, secondary, tertiary)
  • Familiarity with basicity concepts in organic chemistry
  • Knowledge of pKa values and their significance in acid-base chemistry
  • Access to chemical literature and studies, particularly those involving amines
NEXT STEPS
  • Research the pKa values of 1-adamantylamine and 2-adamantylamine
  • Explore the effects of steric hindrance on amine basicity
  • Investigate the structural differences between dimethylamine and trimethylamine
  • Review relevant studies on amine basicity available through academic databases
USEFUL FOR

Chemistry students, organic chemists, and researchers interested in the basicity of amines and the structural factors influencing their reactivity.

KarolinaPL
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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?
 
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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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