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N,N,2,6-Tetramethyl aniline is more basic than N,N-Dimethyl aniline.Why ?

In case of N,N-Dimethyl aniline its dialkyl derivatives the NMe2group is coplanar with benzene ring.  So p-electron (lone pair) on N atom and pi orbitals are remain in the same plane. For this the p-electron on N-atom can delocalized via pi orbital in the benzene ring and its result the electron availability in para position is high and less available at nitrogen atom and hence less basic.

On the other hand , in case of N,N,2,6 tetramethyl aniline(2,6-dimethyl N,N-dimethyl aniline) having two bulky methyl group in ortho position of the benzene ring , the NMe2 group can not remain in the same plane. That is why the p-electron on N-atom cannot delocalized through pi orbital in para position. (due to steric inhibition of resonance)  It is localized at nitrogen atom Thus 2,6-Dimethyl aniline  derivative is more basic.

Related Questions:

  1. What is relative basic strength order 1° amines , 2°amines and 3° amines ? 
  2. Explain:Arrange the following in the increasing order of their acid strength : Methyl amine, Dimethyl amine, Aniline, N-methyl aniline (I.I.T, 1988).
  3. What is Carbylamine test or Isocyanide test ?
  4. What is Hinsberg's reagent and where Hinsberg's test use?
  5. Can we prepare aniline by Gabriel – phthalimide reaction?
  6. N-Ethyl-N-methyl propanamine does not show optical activity why?
  7. What is relative basic strength order 1° amines , 2°amines and 3° amines ? Explain:
  8. Amines are more basic than ammonia why?
  9. Give an explanation for the fact that Guanidine NH=C(CH3)2 is a stronger base than most of amines?
  10. Arrange in correct order of basic Character of aniline, pyrrol, pyridine and piperidine?
  11. What is correct basicity order of pyridine, pyridazine, pyrimidine and pyrazine ?
  12. Give an explanation for the fact that Guanidine NH=C(CH3)2 is a stronger base than most of amines?
  13. Arrange in correct order of basic Character of aniline, pyrrol, pyridine and piperidine?
  14. What is correct basicity order of pyridine, pyridazine, pyrimidine and pyrazine ?
  15. Why pyridine is more basic than Pyrrole?
  16. Why pyrimidine is less basic than pyridine?
  17. Imidazole is more basic than pyridine? Why?
  18. Biological Important of Imidazole and structure:
  19. Pyridine is almost 1 million times less basic than piperidine? Why?
  20. Cyclohexylamine amine is the stronger base than Aniline? Why?
  21. Tetrahydroquinoline amine is the stronger base than Tetrahydroisoquinoline? Why?

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