Crystal structure of pyrogallol[4]arene complex with phosphocholine: A molecular recognition model for phosphocholine through cation-π interaction

Ikuhide Fujisawa, Yuji Kitamura, Rumi Okamoto, Kazutaka Murayama, Ryo Kato, Katsuyuki Aoki

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Single crystal X-ray analysis of the complex formed between pyrogallo[4]arene (1) and phosphocholine (PCh), [Ca(H2O) 3(1)2]·(PCh-) 2·2EtOH·5H2O, a model compound that mimics PCh-receptor recognition in biological systems, has shown that PCh is incorporated into the bowl-shaped cavity of 1 through cation-π interactions between the quaternary cationic trimethylammonium group of PCh and π-rings of 1. The hepta-coordinated [Ca(H2O)3]2+ ion is directly bound to two molecules of 1 through phenolic oxygens to form a dimeric molecule of 1, [1{Ca(H2O)3}1]2+. Conformational data of PCh and its derivatives observed in known crystal structures are compiled, focusing on the conformation about the C-C bond in the P-O-C-C-N + backbone with a reemphasis that the usually observed gauche conformation could be stabilized by an intramolecular N+-C(methyl group)-H⋯O hydrogen bonding.

Original languageEnglish
Pages (from-to)188-193
Number of pages6
JournalJournal of Molecular Structure
Volume1038
DOIs
Publication statusPublished - 2013 Apr 24

Keywords

  • Ca
  • Cation-π interaction
  • Crystal structure
  • Molecular recognition
  • Phosphocholine
  • Pyrogallol[4]arene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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