Bis(benzimidazolium)methane salts: A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes

Sabari Ghosh, Ann Marie Schmiedekamp, Chhanda Mukhopadhyay

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35°C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by 1H NMR and also supported by high resolution mass spectrometry and B3LYP/6- 31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O 1⋯O 4′ and O 3⋯O 2′ across the dibenzo axis of the crown.

Original languageEnglish (US)
Pages (from-to)9826-9835
Number of pages10
JournalTetrahedron
Volume68
Issue number47
DOIs
StatePublished - Nov 25 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Bis(benzimidazolium)methane salts: A potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes'. Together they form a unique fingerprint.

Cite this