Phenolysis of 2, 2′-Biphenoxy Thiophosphinic Chloride: Crystal Structures and DFT Calculations of 2, 2′-Biphenyl 4-<i>Tert</i>-Butylphenyl Thiophosphinate and 2, 2′-Biphenyl 3,4-<i>di</i>-Methylphenyl Thiophosphinate
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In this work, firstly, thiophosphoryl chloride, PSCl<sub>3</sub> (<b>1</b>), with 2,2’-dihydroxybiphenyl, 2,2′-HOC<sub>6</sub>H<sub>4</sub>C<sub>6</sub>H<sub>4</sub>OH (<b>2</b>) were reacted. 2, 2′-biphenoxy thiophosphinic chloride (<b>3</b>) was obtained from this reaction. Second, the reactions of compound (<b>3</b>) with sterically hindered phenol derivatives (<b>4a–4h</b>) were investigated. Novel alkyl-substituted phenyl 2, 2′-biphenyl-thiophosphinate esters (C<sub>6</sub>H<sub>4</sub>O)<sub>2</sub>P(S)OAr (<b>5–12</b>) were obtained from these reactions. Structures of (<b>5–12</b>) were defined by IR, <sup>1</sup>H, <sup>13</sup>C, <sup>31</sup>P NMR spectroscopy, and elemental analysis. The molecular structures of 2, 2′-biphenyl 4-<i>tert-</i>butylphenyl thiophosphinate (<b>11</b>) and 2, 2′-biphenyl 3,4-<i>di</i>-methylphenyl thiophosphinate (<b>6</b>) were determined by single-crystal X-ray diffraction. Density functional theory (DFT) calculations of compounds <b>6</b> and <b>11</b> were made. The theoretical analysis of IR and NMR spectra was performed by DFT based on B3LYP level of theory.
