Synthesis and Dimerization Properties of Cup‐ and Bowl‐shaped Cyclic Trilactams | Zendy

Sartyoungkul Sitanan | Zendy; Yakiyama Yumi | Zendy; Sakurai Hidehiro | Zendy

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Synthesis and Dimerization Properties of Cup‐ and Bowl‐shaped Cyclic Trilactams

Author(s) -

Sartyoungkul Sitanan,

Yakiyama Yumi,

Sakurai Hidehiro

Publication year - 2020

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.202000140

Subject(s) - chemistry , dimer , hydrogen bond , crystallography , solvent , amide , solubility , proton nmr , crystal structure , polymer chemistry , stereochemistry , molecule , organic chemistry

Two chiral trilactams, cup‐shaped (−)‐ 1 and bowl‐shaped (−)‐ 2 , were synthesized. Single crystal X‐ray analysis revealed that (−)‐ 1 formed dimer structure by the formation of three NH⋅⋅⋅O type complementary hydrogen bonds at three amide moieties. The equilibrium constant ( K eq ) and kinetic parameters ▵ H ° and ▵ S ° of the dimer formation phenomenon of (−)‐ 1 were determined by variable temperature proton NMR. Further binding energy calculation on both (−)‐ 1 and (−)‐ 2 dimers confirmed the more favourable formation of (−)‐ 1 dimer than (−)‐ 2 dimer, explaining the significant solubility difference of the two against the less polar solvent, such as CHCl 3 . Trilactam (−)‐ 1 afforded coordination polymer by complexation with Zn 2+ , keeping the capsule‐like structure.

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