Clathrate formation of conformationally rigid Diels-Alder adducts of phencyclone. Role of CH/pi and CH/O interaction in host-host network.

DOI

Bibliographic Information

Other Title
  • Rigidな骨格を有するphencyclone環化付加体のクラスレート形成能．ホスト間ネットワークに対するCH/πおよびCH/O相互作用の役割

Abstract

A novel clathrand having a conformationally-rigid framework was synthesized by the Diels-Alder (DA) reaction of phencyclone with acenaphthylene and the inclusion property was investigated. The host DA adduct enclathrated ketones, cyclic ethers and aromatics. Especially, aromatic guests, such as benzene, were strongly incorporated within the host lattice, and the desolvation temperatures were extremely higher than the boiling point of the pure guests. The crystal structure of the clathrate indicated that weak lattice forces play important roles for host-host and host-guest recognitions, that is, the hosts are linked head-to-tail to form a "column" by the bidentate CH/O hydrogen bonds between phenanthrene ring hydrogens and bridged carbonyl oxygen as well as the pi/pi and CH/pi interactions between the stacking acenaphthene moieties. The aromatic guests are located in "space" between the host columns, in which edge-to-face (CH/pi) interactions between acenaphthene-ring hydrogens and benzene ring are operative. The inclusion behavior of the conformationally-rigid hosts of the same type are discussed on the basis of the thermal analysis, X-ray analysis and the semi-empirical MO calculation (PM6) data.

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Details 詳細情報について

  • CRID
    1390282680531303168
  • NII Article ID
    130004645727
  • DOI
    10.11494/kisoyuki.2011.0.223.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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