A conformational study of [3.3](3,5)pyridinophane

Masahiko Shibahara, Motonori Watanabe, Masahiko Suenaga, Keiko Ideta, Taisuke Matsumoto, Teruo Shinmyozu

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


A variable temperature 1H NMR study of the [3.3](3,5)pyridinophane indicated that the syn(chair/chair) is more stable than syn(chair/boat) by 0.2 kcal/mol in solution, whereas the trimethylene bridges show disorder even at -150 °C in the solid state. A transition state search by ab initio MO calculations suggested two competitive conformational changes for syn(chair/chair)-syn(chair/boat) conversion via a bridge wobble or a ring inversion in the [3.3](3,5)pyridinophane.

Original languageEnglish
Pages (from-to)1340-1344
Number of pages5
JournalTetrahedron Letters
Issue number12
Publication statusPublished - Mar 25 2009

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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