(Salen)tin complexes: Syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO2 and propylene oxide

Huanwang Jing; Smita K. Edulji; Julianne M. Gibbs; Charlotte L. Stern; Hongying Zhou; Son Binh T. Nguyen

doi:10.1021/ic034855z

(Salen)tin complexes: Syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO₂ and propylene oxide

Huanwang Jing, Smita K. Edulji, Julianne M. Gibbs, Charlotte L. Stern, Hongying Zhou, Son Binh T. Nguyen^*

^*Corresponding author for this work

Chemistry

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108 Scopus citations

Abstract

A series of (salen)tin(II) and (salen)tin(IV) complexes was synthesized. The (salen)tin(IV) complexes, (salen)SnX₂ (X = Br and I), were prepared in good yields via the direct oxidation reaction of (salen)tin(II) complexes with Br₂ or I₂. (Salen)SnX₂ successfully underwent the anion-exchange reaction with AgOTf (OTf = trifluoromethanesulfonate) to form (salen)Sn(OTf)₂ and (salen)Sn(X)(OTf) (X = Br). The (salen)Sn(OTf)₂ complex was easily converted to any of the dihalide (salen)SnX₂ compounds using halide salts. All complexes were fully characterized by ¹H NMR spectroscopy, mass spectrometry, and elemental analysis, while some were characterized by ¹³C, ¹⁹F, and ¹¹⁹Sn NMR spectroscopy. Several crystal structures of (salen)tin(II) and (salen)tin(IV) were also determined. Finally, both (salen)tin(II) and (salen)tin(IV) complexes were shown to efficiently catalyze the formation of propylene carbonate from propylene oxide and CO₂. Of the series, (3,3′,5,5′-Br₄-salen) SnBr₂, 3i, was found to be the most effective catalyst (TOF = 524 h^-1).

Original language	English (US)
Pages (from-to)	4315-4327
Number of pages	13
Journal	Inorganic chemistry
Volume	43
Issue number	14
DOIs	https://doi.org/10.1021/ic034855z
State	Published - Jul 12 2004

ASJC Scopus subject areas

Inorganic Chemistry
Physical and Theoretical Chemistry

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10.1021/ic034855z

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@article{8146b0c761994d9d918b262b2470467a,

title = "(Salen)tin complexes: Syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO2 and propylene oxide",

abstract = "A series of (salen)tin(II) and (salen)tin(IV) complexes was synthesized. The (salen)tin(IV) complexes, (salen)SnX2 (X = Br and I), were prepared in good yields via the direct oxidation reaction of (salen)tin(II) complexes with Br2 or I2. (Salen)SnX2 successfully underwent the anion-exchange reaction with AgOTf (OTf = trifluoromethanesulfonate) to form (salen)Sn(OTf)2 and (salen)Sn(X)(OTf) (X = Br). The (salen)Sn(OTf)2 complex was easily converted to any of the dihalide (salen)SnX2 compounds using halide salts. All complexes were fully characterized by 1H NMR spectroscopy, mass spectrometry, and elemental analysis, while some were characterized by 13C, 19F, and 119Sn NMR spectroscopy. Several crystal structures of (salen)tin(II) and (salen)tin(IV) were also determined. Finally, both (salen)tin(II) and (salen)tin(IV) complexes were shown to efficiently catalyze the formation of propylene carbonate from propylene oxide and CO2. Of the series, (3,3′,5,5′-Br4-salen) SnBr2, 3i, was found to be the most effective catalyst (TOF = 524 h-1).",

author = "Huanwang Jing and Edulji, {Smita K.} and Gibbs, {Julianne M.} and Stern, {Charlotte L.} and Hongying Zhou and Nguyen, {Son Binh T.}",

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AU - Jing, Huanwang

AU - Edulji, Smita K.

AU - Gibbs, Julianne M.

AU - Stern, Charlotte L.

AU - Zhou, Hongying

AU - Nguyen, Son Binh T.

PY - 2004/7/12

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N2 - A series of (salen)tin(II) and (salen)tin(IV) complexes was synthesized. The (salen)tin(IV) complexes, (salen)SnX2 (X = Br and I), were prepared in good yields via the direct oxidation reaction of (salen)tin(II) complexes with Br2 or I2. (Salen)SnX2 successfully underwent the anion-exchange reaction with AgOTf (OTf = trifluoromethanesulfonate) to form (salen)Sn(OTf)2 and (salen)Sn(X)(OTf) (X = Br). The (salen)Sn(OTf)2 complex was easily converted to any of the dihalide (salen)SnX2 compounds using halide salts. All complexes were fully characterized by 1H NMR spectroscopy, mass spectrometry, and elemental analysis, while some were characterized by 13C, 19F, and 119Sn NMR spectroscopy. Several crystal structures of (salen)tin(II) and (salen)tin(IV) were also determined. Finally, both (salen)tin(II) and (salen)tin(IV) complexes were shown to efficiently catalyze the formation of propylene carbonate from propylene oxide and CO2. Of the series, (3,3′,5,5′-Br4-salen) SnBr2, 3i, was found to be the most effective catalyst (TOF = 524 h-1).

AB - A series of (salen)tin(II) and (salen)tin(IV) complexes was synthesized. The (salen)tin(IV) complexes, (salen)SnX2 (X = Br and I), were prepared in good yields via the direct oxidation reaction of (salen)tin(II) complexes with Br2 or I2. (Salen)SnX2 successfully underwent the anion-exchange reaction with AgOTf (OTf = trifluoromethanesulfonate) to form (salen)Sn(OTf)2 and (salen)Sn(X)(OTf) (X = Br). The (salen)Sn(OTf)2 complex was easily converted to any of the dihalide (salen)SnX2 compounds using halide salts. All complexes were fully characterized by 1H NMR spectroscopy, mass spectrometry, and elemental analysis, while some were characterized by 13C, 19F, and 119Sn NMR spectroscopy. Several crystal structures of (salen)tin(II) and (salen)tin(IV) were also determined. Finally, both (salen)tin(II) and (salen)tin(IV) complexes were shown to efficiently catalyze the formation of propylene carbonate from propylene oxide and CO2. Of the series, (3,3′,5,5′-Br4-salen) SnBr2, 3i, was found to be the most effective catalyst (TOF = 524 h-1).

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(Salen)tin complexes: Syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO₂ and propylene oxide

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CCDC 246042: Experimental Crystal Structure Determination

CCDC 246044: Experimental Crystal Structure Determination

CCDC 246039: Experimental Crystal Structure Determination

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(Salen)tin complexes: Syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO2 and propylene oxide

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 246042: Experimental Crystal Structure Determination

CCDC 246044: Experimental Crystal Structure Determination

CCDC 246039: Experimental Crystal Structure Determination

Cite this

(Salen)tin complexes: Syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO₂ and propylene oxide