Monday, February 20, 2017

organic chemistry - Do indigo and leuco-indigo have fully conjugated pi systems?


I've just come across a figure indicating the positions of conjugated bonds in indigo and leucoindigo, and I'm quite confused about why both molecules aren't fully conjugated. enter image description here


My reasoning is as follows:



  1. Both carbons above and below the bond are sp2 hybridized and have π electrons.


  2. The carbon to the left is sp2 hybridized and has π electrons, and the nitrogen to the right has a lone pair.

  3. Same as 2.

  4. Same as 1.


I also want to ask about why leuco-indigo isn't planar. According to Wikipedia:



In indigo white, the conjugation is interrupted because the molecule is nonplanar.





No comments:

Post a Comment

periodic trends - Comparing radii in lithium, beryllium, magnesium, aluminium and sodium ions

Apparently the of last four, $\ce{Mg^2+}$ is closest in radius to $\ce{Li+}$. Is this true, and if so, why would a whole larger shell ($\ce{...