Phenolysis of 2, 2′-Biphenoxy Thiophosphinic Chloride: Crystal Structures and DFT Calculations of 2, 2′-Biphenyl 4-Tert-Butylphenyl Thiophosphinate and 2, 2′-Biphenyl 3,4-di-Methylphenyl Thiophosphinate


BEGEÇ S., Yuksel F., Chumakov Y., Alataş S., Kılıç A.

Polycyclic Aromatic Compounds, vol.43, no.8, pp.7426-7438, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 43 Issue: 8
  • Publication Date: 2023
  • Doi Number: 10.1080/10406638.2022.2136721
  • Journal Name: Polycyclic Aromatic Compounds
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, Food Science & Technology Abstracts, Metadex, Pollution Abstracts, Veterinary Science Database, Civil Engineering Abstracts
  • Page Numbers: pp.7426-7438
  • Keywords: Sterically hindered phenols, thiophosphoryl chloride, phosphorothionates, 2,2 '-dihydroxybiphenyl, X-ray crystal structure, DFT calculations, NMR CHEMICAL-SHIFTS
  • Kocaeli University Affiliated: No

Abstract

© 2022 Taylor & Francis Group, LLC.In this work, firstly, thiophosphoryl chloride, PSCl3 (1), with 2,2’-dihydroxybiphenyl, 2,2′-HOC6H4C6H4OH (2) were reacted. 2, 2′-biphenoxy thiophosphinic chloride (3) was obtained from this reaction. Second, the reactions of compound (3) with sterically hindered phenol derivatives (4a–4h) were investigated. Novel alkyl-substituted phenyl 2, 2′-biphenyl-thiophosphinate esters (C6H4O)2P(S)OAr (5–12) were obtained from these reactions. Structures of (5–12) were defined by IR, 1H, 13C, 31P NMR spectroscopy, and elemental analysis. The molecular structures of 2, 2′-biphenyl 4-tert-butylphenyl thiophosphinate (11) and 2, 2′-biphenyl 3,4-di-methylphenyl thiophosphinate (6) were determined by single-crystal X-ray diffraction. Density functional theory (DFT) calculations of compounds 6 and 11 were made. The theoretical analysis of IR and NMR spectra was performed by DFT based on B3LYP level of theory.