1,8-Dimethylnaphthalene-bridged diphosphine ligands: synthesis and structural comparison of their palladium complexes

Ronan M Bellabarba; Colin Hammond; Grant S Forman; Robert P Tooze; Alexandra M Z Slawin

doi:10.1039/b600837b

1,8-Dimethylnaphthalene-bridged diphosphine ligands: synthesis and structural comparison of their palladium complexes

Ronan M Bellabarba, Colin Hammond, Grant S Forman, Robert P Tooze, Alexandra M Z Slawin

4 Citations (Scopus)

Abstract

The synthesis of a new series of ligands with a 1,8-dimethylnaphthalene backbone is reported, 1,8-(R2PCH2)2C10H6, where R = (t)Bu 1 (dbpn), (i)Pr 2 (dippn), Cy 3 (dchpn) and Ph 4 (dphpn). The ligand 1 is structurally characterised by X-ray crystallography. A comparative structural study of the respective (diphosphine)Pd(dba) and (diphosphine)PdCl2 complexes is carried out, comparing the X-ray crystal structures of complexes 6, 7, 8, 10, 11 and 12. It is shown that the geometry at the metal is affected by not only ligand demands, but also by the palladium oxidation state and the electronic properties of the ligands. Two qualitative stability series are also identified: 9 < 10 < 11 approximately 12 is observed, and P2Pd(dba) complexes are more stable than the corresponding P2PdCl2 complexes towards opening of the chelate ring. It is also concluded that the bite angle is heavily influenced by the electron donating properties of the ligand.

Original language	English
Journal	Dalton Transactions (Online)
Issue number	20
Pages (from-to)	2444-9
Number of pages	6
ISSN	1477-9226
DOIs	https://doi.org/10.1039/b600837b
Publication status	Published - 28 May 2006
Externally published	Yes

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Journal Article

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10.1039/b600837b

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title = "1,8-Dimethylnaphthalene-bridged diphosphine ligands: synthesis and structural comparison of their palladium complexes",

abstract = "The synthesis of a new series of ligands with a 1,8-dimethylnaphthalene backbone is reported, 1,8-(R2PCH2)2C10H6, where R = (t)Bu 1 (dbpn), (i)Pr 2 (dippn), Cy 3 (dchpn) and Ph 4 (dphpn). The ligand 1 is structurally characterised by X-ray crystallography. A comparative structural study of the respective (diphosphine)Pd(dba) and (diphosphine)PdCl2 complexes is carried out, comparing the X-ray crystal structures of complexes 6, 7, 8, 10, 11 and 12. It is shown that the geometry at the metal is affected by not only ligand demands, but also by the palladium oxidation state and the electronic properties of the ligands. Two qualitative stability series are also identified: 9 < 10 < 11 approximately 12 is observed, and P2Pd(dba) complexes are more stable than the corresponding P2PdCl2 complexes towards opening of the chelate ring. It is also concluded that the bite angle is heavily influenced by the electron donating properties of the ligand.",

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T1 - 1,8-Dimethylnaphthalene-bridged diphosphine ligands

T2 - synthesis and structural comparison of their palladium complexes

AU - Bellabarba, Ronan M

AU - Hammond, Colin

AU - Forman, Grant S

AU - Tooze, Robert P

AU - Slawin, Alexandra M Z

PY - 2006/5/28

Y1 - 2006/5/28

N2 - The synthesis of a new series of ligands with a 1,8-dimethylnaphthalene backbone is reported, 1,8-(R2PCH2)2C10H6, where R = (t)Bu 1 (dbpn), (i)Pr 2 (dippn), Cy 3 (dchpn) and Ph 4 (dphpn). The ligand 1 is structurally characterised by X-ray crystallography. A comparative structural study of the respective (diphosphine)Pd(dba) and (diphosphine)PdCl2 complexes is carried out, comparing the X-ray crystal structures of complexes 6, 7, 8, 10, 11 and 12. It is shown that the geometry at the metal is affected by not only ligand demands, but also by the palladium oxidation state and the electronic properties of the ligands. Two qualitative stability series are also identified: 9 < 10 < 11 approximately 12 is observed, and P2Pd(dba) complexes are more stable than the corresponding P2PdCl2 complexes towards opening of the chelate ring. It is also concluded that the bite angle is heavily influenced by the electron donating properties of the ligand.

AB - The synthesis of a new series of ligands with a 1,8-dimethylnaphthalene backbone is reported, 1,8-(R2PCH2)2C10H6, where R = (t)Bu 1 (dbpn), (i)Pr 2 (dippn), Cy 3 (dchpn) and Ph 4 (dphpn). The ligand 1 is structurally characterised by X-ray crystallography. A comparative structural study of the respective (diphosphine)Pd(dba) and (diphosphine)PdCl2 complexes is carried out, comparing the X-ray crystal structures of complexes 6, 7, 8, 10, 11 and 12. It is shown that the geometry at the metal is affected by not only ligand demands, but also by the palladium oxidation state and the electronic properties of the ligands. Two qualitative stability series are also identified: 9 < 10 < 11 approximately 12 is observed, and P2Pd(dba) complexes are more stable than the corresponding P2PdCl2 complexes towards opening of the chelate ring. It is also concluded that the bite angle is heavily influenced by the electron donating properties of the ligand.

KW - Journal Article

U2 - 10.1039/b600837b

DO - 10.1039/b600837b

M3 - Journal article

C2 - 16705343

SN - 1477-9234

SP - 2444

EP - 2449

JO - Dalton Transactions (Online)

JF - Dalton Transactions (Online)

IS - 20

ER -

1,8-Dimethylnaphthalene-bridged diphosphine ligands: synthesis and structural comparison of their palladium complexes

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