Molecular Borromean rings

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In

complexes of zinc.[1]

Schematic of a molecular Borromean ring.
Stoddart[1]

The

dative bonds. Because of these interactions, the Borromeate is thermodynamically the most stable reaction product out of potentially many others. As a consequence of all the reactions taking place being equilibria, the Borromeate is the predominant reaction product.[1]

Synthesis of one ring in Borromean ring system from 2,6-diformylpyridine and a diamine in presence of zinc acetate and TFA. The ring-system consists of three such interlocked rings

mechanical bond between the three constituent macrocycles, releasing the other two individual rings.[1][2] A borromeand differs from a [3]catenane in that none of its three macrocycles is concatenated with another other; if one bond in a [3]catenane is broken and a cycle removed, a [2]catenane can remain.[4]

orthogonal
bipyridine groups in Borromeate. Reduction to Borromeand with removal of zinc coordination. Bond cleavage of imine to acetal by action of ethanol

Organic synthesis of this seemingly complex compound is in reality fairly simple; for this reason, the Stoddart group has suggested it as a gram-scale laboratory activity for undergraduate organic chemistry courses.[5]

See also

References

  1. ^
    S2CID 45191675
    .
  2. ^
    PMID 15997275
    .
  3. ISBN 9783527821082
    .
  4. ISBN 9780854042463
    .
  5. doi:10.1021/ed084p855
    .

External links

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