Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

Pravat Mondal, Ephrath Solel, Shubhanjan Mitra, Ehud Keinan, Ofer Reany

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

This study confirms the hypothesis that bambusurils (BUs) with equatorial sulfur atoms cannot assume an anion-binding jigger conformation due to strong intramolecular van der Waals attractive interactions. NMR, X-ray crystallography, and computation with newly synthesized eq-semithio-BU[4] and ax-semiaza-eq-semithio-BU[4]s indicate that they all assume compact conformations. Intramolecular distances and a torsional angle serve as reliable indicators of the conformation of any BU. Chemoselective alkylation at the peripheral (equatorial) thiourea functions provides a convenient entry to novel hetero-BUs.

Original languageEnglish
Pages (from-to)204-208
Number of pages5
JournalOrganic Letters
Volume22
Issue number1
DOIs
StatePublished - 3 Jan 2020
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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