Synthesis and characterization of new N-(diphenylphosphino)-naphthylamine chalcogenides: X-ray structures of (1-NHC 10H 7)P(Se)Ph 2 and Ph 2P(S)OP(S)Ph 2

Harbi Tomah Al-Masri; Abdul-Hamid M. Emwas; Zeyad Al-Talla; Mohamed Al Kordi

doi:10.1080/10426507.2012.668985

Synthesis and characterization of new N-(diphenylphosphino)-naphthylamine chalcogenides: X-ray structures of (1-NHC 10H 7)P(Se)Ph 2 and Ph 2P(S)OP(S)Ph 2

Harbi Tomah Al-Masri, Abdul-Hamid M. Emwas, Zeyad Al-Talla, Mohamed Al Kordi

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The reaction of 1-naphthylamine with one equivalent of chlorodiphenylphosphine in the presence of triethylamine gave the (1-NHC 10H 7)PPh 2 (1) ligand. Refluxing of 1 with elemental sulfur or grey selenium in toluene (1:1 molar ratio) afforded (1-NHC 10H 7)P(S)Ph 2 (2) and (1-NHC 10H 7)P(Se)Ph 2 (3), respectively. Moreover, the byproduct {Ph 2P(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. Copyright © 2012 Taylor and Francis Group, LLC.

Original language	English (US)
Pages (from-to)	1082-1090
Number of pages	9
Journal	Phosphorus, Sulfur, and Silicon and the Related Elements
Volume	187
Issue number	9
DOIs	https://doi.org/10.1080/10426507.2012.668985
State	Published - Sep 2012

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

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10.1080/10426507.2012.668985

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@article{008468b7190147f89e73c497c4227465,

title = "Synthesis and characterization of new N-(diphenylphosphino)-naphthylamine chalcogenides: X-ray structures of (1-NHC 10H 7)P(Se)Ph 2 and Ph 2P(S)OP(S)Ph 2",

abstract = "The reaction of 1-naphthylamine with one equivalent of chlorodiphenylphosphine in the presence of triethylamine gave the (1-NHC 10H 7)PPh 2 (1) ligand. Refluxing of 1 with elemental sulfur or grey selenium in toluene (1:1 molar ratio) afforded (1-NHC 10H 7)P(S)Ph 2 (2) and (1-NHC 10H 7)P(Se)Ph 2 (3), respectively. Moreover, the byproduct {Ph 2P(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. Copyright {\textcopyright} 2012 Taylor and Francis Group, LLC.",

author = "{Tomah Al-Masri}, Harbi and Emwas, {Abdul-Hamid M.} and Zeyad Al-Talla and {Al Kordi}, Mohamed",

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year = "2012",

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doi = "10.1080/10426507.2012.668985",

language = "English (US)",

volume = "187",

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journal = "Phosphorus, Sulfur, and Silicon and the Related Elements",

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Synthesis and characterization of new N-(diphenylphosphino)-naphthylamine chalcogenides: X-ray structures of (1-NHC 10H 7)P(Se)Ph 2 and Ph 2P(S)OP(S)Ph 2. / Tomah Al-Masri, Harbi; Emwas, Abdul-Hamid M.; Al-Talla, Zeyad et al.
In: Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 187, No. 9, 09.2012, p. 1082-1090.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and characterization of new N-(diphenylphosphino)-naphthylamine chalcogenides: X-ray structures of (1-NHC 10H 7)P(Se)Ph 2 and Ph 2P(S)OP(S)Ph 2

AU - Tomah Al-Masri, Harbi

AU - Emwas, Abdul-Hamid M.

AU - Al-Talla, Zeyad

AU - Al Kordi, Mohamed

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2012/9

Y1 - 2012/9

N2 - The reaction of 1-naphthylamine with one equivalent of chlorodiphenylphosphine in the presence of triethylamine gave the (1-NHC 10H 7)PPh 2 (1) ligand. Refluxing of 1 with elemental sulfur or grey selenium in toluene (1:1 molar ratio) afforded (1-NHC 10H 7)P(S)Ph 2 (2) and (1-NHC 10H 7)P(Se)Ph 2 (3), respectively. Moreover, the byproduct {Ph 2P(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. Copyright © 2012 Taylor and Francis Group, LLC.

AB - The reaction of 1-naphthylamine with one equivalent of chlorodiphenylphosphine in the presence of triethylamine gave the (1-NHC 10H 7)PPh 2 (1) ligand. Refluxing of 1 with elemental sulfur or grey selenium in toluene (1:1 molar ratio) afforded (1-NHC 10H 7)P(S)Ph 2 (2) and (1-NHC 10H 7)P(Se)Ph 2 (3), respectively. Moreover, the byproduct {Ph 2P(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. Copyright © 2012 Taylor and Francis Group, LLC.

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DO - 10.1080/10426507.2012.668985

M3 - Article

SN - 1042-6507

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JO - Phosphorus, Sulfur, and Silicon and the Related Elements

JF - Phosphorus, Sulfur, and Silicon and the Related Elements

IS - 9

ER -

Synthesis and characterization of new N-(diphenylphosphino)-naphthylamine chalcogenides: X-ray structures of (1-NHC 10H 7)P(Se)Ph 2 and Ph 2P(S)OP(S)Ph 2

Abstract

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ASJC Scopus subject areas

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CCDC 844302: Experimental Crystal Structure Determination : N-1-Naphthyl-P,P-diphenylphosphinoselenoic amide

CCDC 844303: Experimental Crystal Structure Determination : 1,1,3,3-Tetraphenyldiphosphoxane 1,3-disulfide

Cite this

Synthesis and characterization of new N-(diphenylphosphino)-naphthylamine chalcogenides: X-ray structures of (1-NHC 10H 7)P(Se)Ph 2 and Ph 2P(S)OP(S)Ph 2

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

CCDC 844302: Experimental Crystal Structure Determination : N-1-Naphthyl-P,P-diphenylphosphinoselenoic amide

CCDC 844303: Experimental Crystal Structure Determination : 1,1,3,3-Tetraphenyldiphosphoxane 1,3-disulfide

Cite this