Titrations in non-aqueous media part iii. basicity order of aniline, n-alkky;- and n-aryl-substituted anilines and pyridine in nitrobenzene solvent


Gündüz T., Gündüz N., Kiliç E., KENAR A.

The Analyst, vol.3, no.9, pp.1103-1105, 1986 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 3 Issue: 9
  • Publication Date: 1986
  • Doi Number: 10.1039/an9861101103
  • Journal Name: The Analyst
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1103-1105
  • Keywords: Anilines, Basicity order, Nitrobenzene solvent, Non-aqueous titration, Potentiometric titration
  • Ankara University Affiliated: Yes

Abstract

The relative basicity order of ammonia, pyridine, aniline and N-methyl-, N,N-dimethyl-, N-ethyl-, N,N-diethyl-, N-aryl- and N,N-diaryl-substituted anilines have been determined potentiometrically with perchloric acid in nitrobenzene solvent and found to be NH3 > Py > PhNEt 2 > PhNMe2 > PhNHEt > PhNHMe > PhNH 2 > Ph2NH > Ph3N. This order in general conflicts with the results observed by other workers in either the gas phase or in the condensed phase. N-Alkyl substitution increases the basicity of the aniline, and N-aryl substitution decreases its basicity. Moreover, the number and size of the substituent influence the basicity of aniline. N-Ethyl-substituted anilines are more basic than the corresponding N-methyl-substituted anilines. The position of pyridine in the order is surprising and difficult to interpret.