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

In this work, firstly, thiophosphoryl chloride, PSCl 3 (1), with 2,2'-dihydroxybiphenyl, 2,2′-HOC 6 H 4 C 6 H 4 OH (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...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2023-09, Vol.43 (8), p.7426-7438
Main Authors: Begeç, Saliha, Yuksel, Fatma, Chumakov, Yurii, Alataş, Sümeyya, Kılıç, Adem
Format: Article
Language:English
Subjects:
2,2′-dihydroxybiphenyl
Biphenyl
Chemical analysis
Chlorides
Density functional theory
DFT calculations
Esters
Magnetic resonance spectroscopy
Mathematical analysis
Molecular structure
NMR
NMR spectroscopy
Nuclear magnetic resonance
Phenols
Phenolysis
phosphorothionates
Single crystals
Sterically hindered phenols
Theoretical analysis
thiophosphoryl chloride
X-ray crystal structure
X-ray diffraction
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Summary:In this work, firstly, thiophosphoryl chloride, PSCl 3 (1), with 2,2'-dihydroxybiphenyl, 2,2′-HOC 6 H 4 C 6 H 4 OH (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 (C 6 H 4 O) 2 P(S)OAr (5-12) were obtained from these reactions. Structures of (5-12) were defined by IR, 1 H, 13 C, 31 P 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.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2022.2136721