Structural Analogues of Bioactive Phosphonic Acids: First Crystal Structure Characterization of Phosphonothioic and Boranophosphonic Acids

Yamina Belabassi Department of Chemistry, Texas Christian University, Fort Worth, Texas, USA

Audra F. Gushwa Department of Chemistry, Texas Christian University, Fort Worth, Texas, USA

Anne F. Richards Department of Chemistry, Texas Christian University, Fort Worth, Texas, USA

Jean-Luc Montchamp Department of Chemistry, Texas Christian University, Fort Worth, Texas, USA

Abstract

Phosphonothioic and boranophosphonic acids have been structurally characterized for the first time by single X-ray crystallography. These two functional groups, and the corresponding phosphonic acid, were all conveniently synthesized in high yields from trityl H-phosphinic acid (Ph₃CPO₂H₂). The resulting trityl-substituted series: Ph₃CP(O)(OH)₂, Ph₃CP(S)(OH)₂, Ph₃CP(O)(BH₃ ⁻)(OH)]LH⁺ (L = Lewis base) is fully characterized by spectroscopic methods, and the structural characteristics are compared. The results indicate that boranophosphonic acids should be investigated anytime a bioactive phosphonic acid has been identified. The solid state arrangements of the synthesized compounds are also discussed.

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Acknowledgments

Financial support of this research by The Robert A Welch Foundation (P0176, AFG, AFR), and by the National Institute of General Medical Sciences/NIH (1R01GM067610, YB, JLM) is gratefully acknowledged.

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