Synthesis and Characterization of New N-(Diphenylphosphino)-Naphthylamine Chalcogenides: X-Ray Structures of (1-NHC10H7)P(Se)Ph2 and Ph2P(S)OP(S)Ph2

Harbi Tomah Al‐Masri; Abdul‐Hamid Emwas; Zeyad A. Al‐Talla; Mohamed H. Alkordi

doi:10.1080/10426507.2012.668985

June 19, 2012Phosphorus, sulfur, and silicon and the related elements

Synthesis and Characterization of New N-(Diphenylphosphino)-Naphthylamine Chalcogenides: X-Ray Structures of (1-NHC10H7)P(Se)Ph2 and Ph2P(S)OP(S)Ph2

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Key Points

To synthesize novel N-(diphenylphosphino)-naphthylamine derivatives and their corresponding chalcogenide adducts, and to structurally characterize the resulting chemical species.
Coupled 1-naphthylamine with chlorodiphenylphosphine in the presence of triethylamine to synthesize the parent aminophosphine ligand (1).
Refluxed ligand 1 in toluene with elemental sulfur or grey selenium in a 1:1 molar ratio to produce sulfur (2) and selenium (3) chalcogenides, alongside an isolated byproduct (4).
Characterized all compounds using multinuclear (1H, 13C, 31P, 77Se) NMR spectroscopy, mass spectrometry, and elemental analysis, with single-crystal X-ray diffraction performed for 3 and 4.
Successfully isolated the new chalcogenide compounds (1-NHC10H7)P(S)Ph2 (2) and (1-NHC10H7)P(Se)Ph2 (3) from direct chalcogenation of the precursor ligand.
Identified and separated the oxide-bridged diphosphine disulfide byproduct {Ph2P(S)}2O (4) from the sulfur oxidation reaction mixture.
Resolved the solid-state molecular structures and coordination geometries of compounds 3 and 4 via X-ray crystallographic analysis.

Implication

Experimental study demonstrates the synthesis and single-crystal structures of new naphthylamine-based phosphine chalcogenides, highlighting novel coordination frameworks for organophosphorus...

Abstract

The reaction of 1-naphthylamine with one equivalent of chlorodiphenylphosphine in the presence of triethylamine gave the (1-NHC10H7)PPh2 (1) ligand. Refluxing of 1 with elemental sulfur or grey selenium in toluene (1:1 molar ratio) afforded (1-NHC10H7)P(S)Ph2 (2) and (1-NHC10H7)P(Se)Ph2 (3), respectively. Moreover, the byproduct {Ph2P(S)}2O (4) was isolated from the reaction of 1 with elemental sulfur. Compounds 1–3 were identified and characterized by multinuclear (1H, 13C, 31P, 77Se) NMR spectroscopy, mass spectrometry, and elemental analysis. Crystal structure determinations of 3 and 4 were carried out.

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Al‐Masri et al. (2012) studied this question.

synapsesocial.com/papers/6a9be2157ef7c4cee06bee9d https://doi.org/10.1080/10426507.2012.668985

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Synthesis and Characterization of New N-(Diphenylphosphino)-Naphthylamine Chalcogenides: X-Ray Structures of (1-NHC10H7)P(Se)Ph2 and Ph2P(S)OP(S)Ph2

Key Points

Implication

Abstract

Discussion

Cite This Study

Synthesis and Characterization of New N-(Diphenylphosphino)-Naphthylamine Chalcogenides: X-Ray Structures of (1-NHC10H7)P(Se)Ph2 and Ph2P(S)OP(S)Ph2

Key Points

Implication

Abstract

Discussion

Cite This Study

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