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.
My reasoning is as follows:
- Both carbons above and below the bond are sp2 hybridized and have π electrons.
- The carbon to the left is sp2 hybridized and has π electrons, and the nitrogen to the right has a lone pair.
- Same as 2.
- 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.
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