4.5 Article

Synthesis and Solid-State Structure of (4-Hydroxy-3,5-diiodophenyl) phosphine Oxides. Dimeric Motifs with the Assistance of O-H•••O=P Hydrogen Bonds

Journal

CURRENT ORGANIC CHEMISTRY
Volume 19, Issue 5, Pages 469-474

Publisher

BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1385272819666141231000247

Keywords

Halogen bonding; hydrogen bonding; iodination; phosphine oxides; X-ray crystallography

Funding

  1. American Chemical Society Petroleum Research Fund (PRF) [52858]
  2. NSF [CHE-0821487, CHE-0722547, CHE-1048719]
  3. OU Research Excellence Fund
  4. Provost's Undergraduate Student Research Award

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(4-Hydroxy-3,5-diiodophenyl)diphenylphosphine oxide, bis(4-hydroxy-3,5-diiodophenyl)(phenyl) phosphine oxide, and tris(4-hydroxy-3,5-diiodophenyl)phosphine oxide were obtained via iodination reactions of corresponding mono-, bis-, and tris(4-hydroxyphenyl)phosphine oxides. Single-crystal X-ray diffraction studies showed each homologue forms O-H center dot center dot center dot O=P and pi-stacking interactions with neighboring molecules to give inversion related dimeric motifs.

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