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Rule K: Where multiple bond closure symbols occur on the same atom, symbols describing bond openings are listed first, ordered by the canonical label of the corresponding neighbour atom (smallest first), followed by those describing bond closings, in the order in which the corresponding bond opening was made (i.e. the output order of the corresponding neighbour atom).
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An analysis of the shapes adopted by species with multiple bonds suggests that each multiple bond can be treated as a single "superpair" of electrons.
Heteronuclear multiple bond connectivity.
Rule I: Cis/trans stereochemistry at a bond closure should only be indicated at the bond closure symbol attached to the double bond.
For every bond closure in a SMILES string, two bond closure symbols are included indicating the start and end of the bond, or the bond opening and bond closing.
In other words, bond closure symbols should be reused once available.
Placing a stereo symbol at the bond closure symbol distant from the double bond should be avoided as it may lead to difficulties in interpretation: Rule I: Cis/trans stereochemistry at a bond closure should only be indicated at the bond closure symbol attached to the double bond.
The most straightforward way to traverse the graph is using a depth-first search (this minimises bond closure symbols).
Fig. 5 Heteronuclear multiple bond correlation (HMBC) of DNPH-glucose.
Rule J: When choosing a bond closure symbol, the lowest value available should be used (where 1 is the lowest possible value).
NMR (heteronuclear multiple bond correlation through the double bond) confirms one GMA per chain terminus.
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