Synthesis, spectroscopic, and structural characterization of new functionalized gem-bisphosphonate complexes of tin(IV) chloride

Marwa Yahyaoui; Med Abderrahmane Sanhoury; Cameron L. Carpenter-Warren; Alexandra Martha Zoya Slawin; J Derek Woollins; Soufiane Touil; Ali Samarat

doi:10.1016/j.cdc.2018.11.009

Synthesis, spectroscopic, and structural characterization of new functionalized gem-bisphosphonate complexes of tin(IV) chloride

Marwa Yahyaoui, Med Abderrahmane Sanhoury, Cameron L. Carpenter-Warren, Alexandra Martha Zoya Slawin, J Derek Woollins, Soufiane Touil, Ali Samarat

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

Abstract

Bisphosphonates of the types X(P(O)(OEt)₂)₂ (X = CH₂=C (1a), CNCH₂CH (1b) and PhCH₂NCH₂CH (1c)) react with SnCl₄ in anhydrous dichloromethane to produce the new tin(IV) adducts [SnCl₄(1a)] (2a), [SnCl₄(1b)] (2b) and [SnCl₄(1c)] (2c) in 72-80% yields. These complexes were characterized using IR, multinuclear (¹H, ¹³C, ³¹P, ¹¹⁹Sn) NMR spectroscopy, elemental analysis, and in one case by single crystal X-ray diffraction. The NMR data show that the bisphosphonate ligands are coordinated to the tin center in a bidentate fashion forming cis octahedral tin complexes. Furthermore, the X-ray structure of complex 2b reveals that the bisphosphonate ligand is coordinated in a bidentate manner to the metal center in a distorted octahedral arrangement with Sn-O-P bond angles in the range 135.95(16)–137.99(18)°. The P=O and Sn-O bond lengths of 1.495(3)-1.497(3) and 2.134(3)-2.146(2) Å, respectively are in the order expected for phosphonate tin(IV) complexes. The results are discussed and compared with closely related analogues.

Original language	English
Journal	Chemical Data Collections
Volume	In press
Early online date	22 Nov 2018
DOIs	https://doi.org/10.1016/j.cdc.2018.11.009
Publication status	E-pub ahead of print - 22 Nov 2018

Keywords

gem-Bisphosphonates
tin(IV) chloride
119Sn and 31P NMR
X-ray structure

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10.1016/j.cdc.2018.11.009

Woollins_2018_CDC_SynthesisGem_AAM
© 2018 Published by Elsevier B.V. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.cdc.2018.11.009
Accepted author manuscript, 1.27 MBLicence: CC BY-NC-ND

Synthesis, spectroscopic, and structural characterization of new functionalized gem-bisphosphonate complexes of tin(IV) chloride (dataset)
Yahyaoui, M. (Creator), Sanhoury, M. A. (Creator), Carpenter-Warren, C. L. (Creator), Slawin, A. M. Z. (Creator), Woollins, J. D. (Creator), Touil, S. (Creator) & Samarat, A. (Creator), Cambridge Crystallographic Data Centre, 15 Aug 2018
https://dx.doi.org/10.5517/ccdc.csd.cc20hv5k
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@article{94955f0750bd468ea30999f90b1e2231,

title = "Synthesis, spectroscopic, and structural characterization of new functionalized gem-bisphosphonate complexes of tin(IV) chloride",

abstract = "Bisphosphonates of the types X(P(O)(OEt)2)2 (X = CH2=C (1a), CNCH2CH (1b) and PhCH2NCH2CH (1c)) react with SnCl4 in anhydrous dichloromethane to produce the new tin(IV) adducts [SnCl4(1a)] (2a), [SnCl4(1b)] (2b) and [SnCl4(1c)] (2c) in 72-80% yields. These complexes were characterized using IR, multinuclear (1H, 13C, 31P, 119Sn) NMR spectroscopy, elemental analysis, and in one case by single crystal X-ray diffraction. The NMR data show that the bisphosphonate ligands are coordinated to the tin center in a bidentate fashion forming cis octahedral tin complexes. Furthermore, the X-ray structure of complex 2b reveals that the bisphosphonate ligand is coordinated in a bidentate manner to the metal center in a distorted octahedral arrangement with Sn-O-P bond angles in the range 135.95(16)–137.99(18)°. The P=O and Sn-O bond lengths of 1.495(3)-1.497(3) and 2.134(3)-2.146(2) {\AA}, respectively are in the order expected for phosphonate tin(IV) complexes. The results are discussed and compared with closely related analogues.",

keywords = "gem-Bisphosphonates, tin(IV) chloride, 119Sn and 31P NMR, X-ray structure",

author = "Marwa Yahyaoui and Sanhoury, {Med Abderrahmane} and Carpenter-Warren, {Cameron L.} and Slawin, {Alexandra Martha Zoya} and Woollins, {J Derek} and Soufiane Touil and Ali Samarat",

note = "The authors are grateful to the Tunisian Ministry of High Education and Scientific Research and Technology for financial support of this research ",

year = "2018",

month = nov,

day = "22",

doi = "10.1016/j.cdc.2018.11.009",

language = "English",

volume = "In press",

journal = "Chemical Data Collections",

}

TY - JOUR

T1 - Synthesis, spectroscopic, and structural characterization of new functionalized gem-bisphosphonate complexes of tin(IV) chloride

AU - Yahyaoui, Marwa

AU - Sanhoury, Med Abderrahmane

AU - Carpenter-Warren, Cameron L.

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, J Derek

AU - Touil, Soufiane

AU - Samarat, Ali

N1 - The authors are grateful to the Tunisian Ministry of High Education and Scientific Research and Technology for financial support of this research

PY - 2018/11/22

Y1 - 2018/11/22

N2 - Bisphosphonates of the types X(P(O)(OEt)2)2 (X = CH2=C (1a), CNCH2CH (1b) and PhCH2NCH2CH (1c)) react with SnCl4 in anhydrous dichloromethane to produce the new tin(IV) adducts [SnCl4(1a)] (2a), [SnCl4(1b)] (2b) and [SnCl4(1c)] (2c) in 72-80% yields. These complexes were characterized using IR, multinuclear (1H, 13C, 31P, 119Sn) NMR spectroscopy, elemental analysis, and in one case by single crystal X-ray diffraction. The NMR data show that the bisphosphonate ligands are coordinated to the tin center in a bidentate fashion forming cis octahedral tin complexes. Furthermore, the X-ray structure of complex 2b reveals that the bisphosphonate ligand is coordinated in a bidentate manner to the metal center in a distorted octahedral arrangement with Sn-O-P bond angles in the range 135.95(16)–137.99(18)°. The P=O and Sn-O bond lengths of 1.495(3)-1.497(3) and 2.134(3)-2.146(2) Å, respectively are in the order expected for phosphonate tin(IV) complexes. The results are discussed and compared with closely related analogues.

AB - Bisphosphonates of the types X(P(O)(OEt)2)2 (X = CH2=C (1a), CNCH2CH (1b) and PhCH2NCH2CH (1c)) react with SnCl4 in anhydrous dichloromethane to produce the new tin(IV) adducts [SnCl4(1a)] (2a), [SnCl4(1b)] (2b) and [SnCl4(1c)] (2c) in 72-80% yields. These complexes were characterized using IR, multinuclear (1H, 13C, 31P, 119Sn) NMR spectroscopy, elemental analysis, and in one case by single crystal X-ray diffraction. The NMR data show that the bisphosphonate ligands are coordinated to the tin center in a bidentate fashion forming cis octahedral tin complexes. Furthermore, the X-ray structure of complex 2b reveals that the bisphosphonate ligand is coordinated in a bidentate manner to the metal center in a distorted octahedral arrangement with Sn-O-P bond angles in the range 135.95(16)–137.99(18)°. The P=O and Sn-O bond lengths of 1.495(3)-1.497(3) and 2.134(3)-2.146(2) Å, respectively are in the order expected for phosphonate tin(IV) complexes. The results are discussed and compared with closely related analogues.

KW - gem-Bisphosphonates

KW - tin(IV) chloride

KW - 119Sn and 31P NMR

KW - X-ray structure

U2 - 10.1016/j.cdc.2018.11.009

DO - 10.1016/j.cdc.2018.11.009

M3 - Article

VL - In press

JO - Chemical Data Collections

JF - Chemical Data Collections

ER -

Synthesis, spectroscopic, and structural characterization of new functionalized gem-bisphosphonate complexes of tin(IV) chloride

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Keywords

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Synthesis, spectroscopic, and structural characterization of new functionalized gem-bisphosphonate complexes of tin(IV) chloride (dataset)

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