NDLI: Olefin coordination in copper(I) complexes of <i>bis</i>(2-pyridyl)amine

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Olefin coordination in copper(I) complexes of bis(2-pyridyl)amine

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Olefin coordination in copper(I) complexes of bis(2-pyridyl)amine

Content Provider	Royal Society of Chemistry (RSC)
Author	Allen, John J. Barron, Andrew R.
Copyright Year	2009
Abstract	Complexes of the type [Cu(H-dpa)(olefin)]BF4 for ethylene (1), propylene (2), 1-butene (3), 1-hexene (4), 1-octene (5), cis-2-octene (6), trans-2-octene (7), cis-3-octene (8), trans-3-octene (9), 2-norbornylene (10), 1,5-cyclooctadiene (11), styrene (12), cis-stilbene (13), trans-stilbene (14), and Ph2CCH2 (15) have been prepared and characterized by 1H and 13C NMR, FTIR, and TGA. The crystal structures have been determined for compounds 5, 6, 8, and 10–13. With the exception of compound 11, copper atoms in each complex are coordinated to the two pyridine nitrogen atoms and the appropriate olefin; consistent with a pseudo three-coordinate Cu(I) cation. Compound 11 has a second weaker π-interaction resulting in a distorted tetrahedral geometry. Steric hindrance between the olefin and H-dpa manifests as both a twisting of the olefin out of the plane of the H-dpa ligand and a concomitant folding of the H-dpa ligand. The shifts in the νN-H IR spectral band for H-dpa ligand are consistent with the formation of N–H⋯F hydrogen bonded interactions observed in the crystal structures. The 1H and 13C NMR spectra of [Cu(H-dpa)(olefin)]BF4 exhibit an upfield shift in the olefin signal as compared to free olefin. A comparison of the Δδ values for terminal olefins shows that the similarity of binding for H2CCHR (R = CnH2n+1, n = 1–6) mitigates any preferential complexation of various terminal olefins using the H-dpa ligand. For octenes there is a significant difference in binding between a terminal and internal olefin, but there is little preference between binding for different internal olefins and only a modest difference between the cis and trans isomers of the same olefin. A good correlation exists between the 1H NMR Δδ values and the TGA data, confirming that the shift of the olefin NMR resonances upon coordination is associated with the binding strength of the complex. Ab initio calculations using four different method/basis set combinations on the structure of [Cu(H-dpa)(1-octene)]+ were compared with the crystal structure.
Starting Page	878
Ending Page	890
Page Count	13
File Format	HTM / HTML PDF
ISSN	14779226
Volume Number	0
Issue Number	5
Journal	Dalton Transactions
DOI	10.1039/b814829e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Alkene Ethylene Propene 1-Butene 1-Hexene 1-Octene Octene 5-Cyclooctadiene Styrene (Z)-Stilbene Nuclear magnetic resonance Copper Pyridine Nitrogen Ion Pi interaction Molecular geometry Steric effects Ligand Hydrogen bond Ab initio Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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