Dearomtizing

User ceb580837f

20-04-2006 16:09:03

Dear Sirs,


unfortunately I fear that your method "dearomatize" of the class "molecule" is not handling all molecules correctly!





If I try to dearomatize pyrrole (input-smiles c1cccn1) the given output in smiles is identical and not as I hoped C1=CC=CN1! An identical result is obtained for pyrrazole (c1ccnn1).





Remarkeble is the fact the oxygen analogue (c1ccco1) is dearomtized correctly to O1C=CC=C1. As well as it is true for c1ccno1 which is converted correctly to O1C=CC=N1.


Which is also through for pyridine (c1ccccn1) which leads to C1=CC=NC=C1.





So, I think the error is related to the five-membered aromatics with a nitrogen!





Hopefully it helps you in optimising your work!





With kind regards,


Ruud van Deursen

ChemAxon d76e6e95eb

20-04-2006 16:51:01

The correct SMILES of pyrrole is "c1cc[nH]c1" and not "c1cccn1". Look at chapter 3.3.3 here: http://www.daylight.com/dayhtml/doc/theory/theory.smiles.html. The situation is similar for all nitrogen containing aromatic rings, the hydrogen must be indicated in the SMILES string, otherwise your input string is corrupt. Which software generated those SMILES strings?