Geometry of imidacloprid is E Form, this record is a muddle of any geography, correct BRN for this is 8069674 Looking at this record - the imidazolidinimine group is basically a masked guanidine and so the double bond can move to create a number of tautomers. The registration of the compound in ChemSpider accepts that this can move and many of the tautomers all map onto the same record. In terms of reflecting the actual nature of the compound this behaviour is ideal as it actually matches the real world behaviour of the compound - but from the perspective of naming it does mean that names that have encoded stereochemistry can appear to be incorrectly associated with the particular depiction. This is not perfect - but for the purposes of discovery of information - it would be valid to accept names that express a valid tautomer but do not match the structure depiction perfectly.
Oct 25 2012 9:02AM
Normal
Acknowledged
The SMILES and Std. InChI do not resemble the structure shown in the graphic, but a tautomeric form
Best regards
Martin The InChI is definitely correct for this structure (as it is the key identifier for the database) - The InChI algorithm contains code that detects certain types of tautomer and collapses all of these tautomers to the same identifier. There are settings that avoid that but these are not used in the StdInChI.
(for more details, see: http://www.inchi-trust.org/fileadmin/user_upload/html/inchifaq/inchi-faq.html#6)