(N-Benzyl-bis-N′,N″-salicylidene)-cis-1,3,5-triaminocyclohex ane copper(ii): a novel catalyst for the aerobic oxidation of benzyl alcohol

Nairn, Alison K., Archibald, Stephen J., Bhalla, Rajiv, Gilbert, Bruce C., MacLean, Elizabeth J., Teat, Simon J. and Walton, Paul H. (2006) (N-Benzyl-bis-N′,N″-salicylidene)-cis-1,3,5-triaminocyclohex ane copper(ii): a novel catalyst for the aerobic oxidation of benzyl alcohol. Dalton Transactions, 2006 1: 172-176. doi:10.1039/b512296c

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Author Nairn, Alison K.
Archibald, Stephen J.
Bhalla, Rajiv
Gilbert, Bruce C.
MacLean, Elizabeth J.
Teat, Simon J.
Walton, Paul H.
Title (N-Benzyl-bis-N′,N″-salicylidene)-cis-1,3,5-triaminocyclohex ane copper(ii): a novel catalyst for the aerobic oxidation of benzyl alcohol
Formatted title
(N-Benzyl-bis-N′,N″-salicylidene)-cis-1,3,5-triaminocyclohex ane copper(II): a novel catalyst for the aerobic oxidation of benzyl alcohol
Journal name Dalton Transactions   Check publisher's open access policy
ISSN 1477-9226
Publication date 2006
Sub-type Article (original research)
DOI 10.1039/b512296c
Open Access Status File (Publisher version)
Volume 2006
Issue 1
Start page 172
End page 176
Total pages 5
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Abstract Reaction of Cu(BF4)2·6H2O with the N3O2 donor ligand H2L (where H2L = N-benzyl-N′,N″-di-tert-butyl-disalicyl-triaminocyclohexane) results in the formation of a novel CuIIL complex, 1. X-Ray crystallography of 1 shows the CuII centre coordinated by two phenolate oxygens and two imine nitrogens in a distorted square plane with an elongated bond to the amine nitrogen (2.512 Å) in the axial position. EPR spectroscopy of 1 gives g values of g1 = 2.277, g2 = 2.100, g3 = 2.025, and A1 = 15.6 mT which are consistent with the distorted square pyramidal coordination environment determined from the X-ray structure. UV/visible and electrochemical analysis of 1 shows that it undergoes two reversible processes assigned to the successive oxidation of the phenolate oxygens to phenoxyl radicals, the first at E1/2 = 0.89 V (ΔE = 81 mV, vs. Ag/AgCl) and the second at E1/2 = 1.13V (ΔE = 84 mV, vs. Ag/AgCl). Chemical oxidation of 1 results in the formation of a species, assigned as [1]+ which is EPR silent due to antiferromagnetic coupling between the CuII centre and the bound phenoxyl radical. The oxidised species catalyses the oxidation of benzyl alcohol to benzaldehyde.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Centre for Advanced Imaging Publications
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