Synthesis of the Trans-bidentate Ligand 1,2-Bis(Quinolin-2-ylethynyl)Benzene and the X-ray Crystal Structure of Its Complex with Palladium(II) Chloride

Luke L. Hair; Megan M. Smart; Colin D. McMillen; Nicholas A. Ribeiro; Jared A. Pienkos

doi:10.1007/s10870-023-00988-y

Synthesis of the Trans-bidentate Ligand 1,2-Bis(Quinolin-2-ylethynyl)Benzene and the X-ray Crystal Structure of Its Complex with Palladium(II) Chloride

Luke L. Hair, Megan M. Smart, Colin D. McMillen, Nicholas A. Ribeiro, Jared A. Pienkos

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

Abstract

A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene, was synthesized and coordinated to PdCl₂. The structure of the acetonitrile solvate of this species was determined by single-crystal X-ray diffraction. The complex crystallizes in the orthorhombic space group Ibam, with a = 25.0726(18) Å, b = 11.7373(6) Å, and c = 18.9700(10) Å in a layered structure. When bound to 1,2-bis(quinolin-2-ylethynyl)benzene, the Pd(II) metal center displays a distorted square planar geometry. This coordination complex was compared to PdCl₂-coordinated 1,2-bis(2-pyridylethynyl)benzene, a previously reported trans-bidentate ligand. Structural comparison indicated that the binding pocket for these two trans-bidentate ligands are similar, though the 1,2-bis(quinolin-2-ylethynyl)benzene ligand is somewhat more planar. Graphical Abstract: A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene (BQEB), was synthesized and coordinated to PdCl₂.[Figure not available: see fulltext.]

Original language	English
Pages (from-to)	500-506
Number of pages	7
Journal	Journal of Chemical Crystallography
Volume	53
Issue number	4
DOIs	https://doi.org/10.1007/s10870-023-00988-y
State	Published - Dec 2023
Externally published	Yes

Funding

We thank the Grote Research Fund at the University of Tennessee at Chattanooga and funding administered by the ACS Petroleum Research Fund (61868-UNI3). We would like to thank Berhane Temelso and Sarah L. McDarmont for their input during the preparation of this manuscript and Madelyn R. Shevlin and John P. Lee for their assistance with the synthetic chemistry.

Funders	Funder number
American Chemical Society Petroleum Research Fund	61868-UNI3
University of Tennessee

Keywords

Crystal structure
Ligand
Palladium complex
Trans-N,N-chelating
Trans-bidentate

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10.1007/s10870-023-00988-y

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title = "Synthesis of the Trans-bidentate Ligand 1,2-Bis(Quinolin-2-ylethynyl)Benzene and the X-ray Crystal Structure of Its Complex with Palladium(II) Chloride",

abstract = "A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene, was synthesized and coordinated to PdCl2. The structure of the acetonitrile solvate of this species was determined by single-crystal X-ray diffraction. The complex crystallizes in the orthorhombic space group Ibam, with a = 25.0726(18) {\AA}, b = 11.7373(6) {\AA}, and c = 18.9700(10) {\AA} in a layered structure. When bound to 1,2-bis(quinolin-2-ylethynyl)benzene, the Pd(II) metal center displays a distorted square planar geometry. This coordination complex was compared to PdCl2-coordinated 1,2-bis(2-pyridylethynyl)benzene, a previously reported trans-bidentate ligand. Structural comparison indicated that the binding pocket for these two trans-bidentate ligands are similar, though the 1,2-bis(quinolin-2-ylethynyl)benzene ligand is somewhat more planar. Graphical Abstract: A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene (BQEB), was synthesized and coordinated to PdCl2.[Figure not available: see fulltext.]",

keywords = "Crystal structure, Ligand, Palladium complex, Trans-N,N-chelating, Trans-bidentate",

author = "Hair, {Luke L.} and Smart, {Megan M.} and McMillen, {Colin D.} and Ribeiro, {Nicholas A.} and Pienkos, {Jared A.}",

note = "Publisher Copyright: {\textcopyright} 2023, This is a U.S. Government work and not under copyright protection in the US; foreign copyright protection may apply.",

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T1 - Synthesis of the Trans-bidentate Ligand 1,2-Bis(Quinolin-2-ylethynyl)Benzene and the X-ray Crystal Structure of Its Complex with Palladium(II) Chloride

AU - Hair, Luke L.

AU - Smart, Megan M.

AU - McMillen, Colin D.

AU - Ribeiro, Nicholas A.

AU - Pienkos, Jared A.

PY - 2023/12

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N2 - A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene, was synthesized and coordinated to PdCl2. The structure of the acetonitrile solvate of this species was determined by single-crystal X-ray diffraction. The complex crystallizes in the orthorhombic space group Ibam, with a = 25.0726(18) Å, b = 11.7373(6) Å, and c = 18.9700(10) Å in a layered structure. When bound to 1,2-bis(quinolin-2-ylethynyl)benzene, the Pd(II) metal center displays a distorted square planar geometry. This coordination complex was compared to PdCl2-coordinated 1,2-bis(2-pyridylethynyl)benzene, a previously reported trans-bidentate ligand. Structural comparison indicated that the binding pocket for these two trans-bidentate ligands are similar, though the 1,2-bis(quinolin-2-ylethynyl)benzene ligand is somewhat more planar. Graphical Abstract: A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene (BQEB), was synthesized and coordinated to PdCl2.[Figure not available: see fulltext.]

AB - A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene, was synthesized and coordinated to PdCl2. The structure of the acetonitrile solvate of this species was determined by single-crystal X-ray diffraction. The complex crystallizes in the orthorhombic space group Ibam, with a = 25.0726(18) Å, b = 11.7373(6) Å, and c = 18.9700(10) Å in a layered structure. When bound to 1,2-bis(quinolin-2-ylethynyl)benzene, the Pd(II) metal center displays a distorted square planar geometry. This coordination complex was compared to PdCl2-coordinated 1,2-bis(2-pyridylethynyl)benzene, a previously reported trans-bidentate ligand. Structural comparison indicated that the binding pocket for these two trans-bidentate ligands are similar, though the 1,2-bis(quinolin-2-ylethynyl)benzene ligand is somewhat more planar. Graphical Abstract: A new trans-bidentate ligand, 1,2-bis(quinolin-2-ylethynyl)benzene (BQEB), was synthesized and coordinated to PdCl2.[Figure not available: see fulltext.]

KW - Crystal structure

KW - Ligand

KW - Palladium complex

KW - Trans-N,N-chelating

KW - Trans-bidentate

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Synthesis of the Trans-bidentate Ligand 1,2-Bis(Quinolin-2-ylethynyl)Benzene and the X-ray Crystal Structure of Its Complex with Palladium(II) Chloride

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Keywords

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