I know that amino groups (nitrogen with single bonds with hydrogen and/or carbon) are basic.

I wanted to know if azo groups ($\ce{R-N=N-R}$) are similarly basic.

I searched online but couldn't find any reference whatsoever.

And I'm not sure if being double bonded with another nitrogen might or might not change the basicity of the nitrogen.

  • 4
    $\begingroup$ Not basic at all, pKa -2.95 en.wikipedia.org/wiki/Azobenzene $\endgroup$
    – Waylander
    Nov 9, 2021 at 18:08
  • $\begingroup$ Nitrogen is strongly electron withdrawing, so... As one can expect situation is similar, if not worse for N2, O2 and CO2 in particular. $\endgroup$
    – Mithoron
    Nov 9, 2021 at 18:36
  • $\begingroup$ @Waylander that is slightly unfair, as the nitrogen is conjugated to aromatic rings which weaken its basicity. Then again, since such conjugation is generally needed to stabilize azo compounds at all against decomposition to radicals, we can argue that the azo function is for all practical purposes not an aqueous B-L base. $\endgroup$ Mar 6 at 1:42


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.