#874 aromaticity of cyclobutenedione

2.0_alpha-beta
open
nobody
None
1
2014-03-15
2013-04-25
Jeff Janes
No

If you have a cyclobutenedione drawn in the aromatic form, openbabel 2.3.2 will canonicalize it to cyclobutadione, hydrogenating the double bond in the ring.

echo 'CCOc1c(NCC)c(=O)c1=O'| obabel -ismi -ocan
CCNC1C(=O)C(=O)C1OCC

I don't know if cyclobutenedione is really aromatic or not, but if it is drawn as aromatic, then it can't have two sp3 carbons in the ring the way the canonicalization has it

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