Document Detail

Preparation and characterization of asymmetric alpha-alkoxy dipyrrin ligands and their metal complexes.
MedLine Citation:
PMID:  17325783     Owner:  NLM     Status:  MEDLINE    
Asymmetric alpha-substituted dipyrrins have been synthesized and characterized. The compounds were formed by a metal mediated reaction involving a single alkoxy group substituted into the alpha-position of an alpha,beta-unsubstituted dipyrrin. An alpha-methoxy dipyrrin, 5-(4-cyanophenyl)-1-methoxydipyrrin (alpha-OMe-4-cydpm), was prepared from 5-(4-cyanophenyl)-4,6-dipyrromethane. Methoxy, ethoxy, and propoxy derivatives (alpha-OMe-4-mecdpm, alpha-OEt-4-mecdpm, alpha-OPr-4-mecdpm) of 5-(4-methoxycarbonylphenyl)-4,6-dipyrromethane have also been prepared. A homoleptic, bis(1-methoxy)dipyrrinato zinc(II) complex, [Zn(alpha-OMe-4-mecdpm)(2)], has been synthesized, as has a heteroleptic cobalt(III) complex with one alpha-OMe-4-cydpm ligand and two unsubstituted 5-(4-cyanophenyl)dipyrrin (4-cydpm) ligands ([Co(alpha-OMe-4-cydpm)(4-cydpm)(2)]). The rotational barrier of the meso-aryl substituent of [Zn(alpha-OMe-4-mecdpm)(2)] was found to be 17.3 kcal mol(-1) by variable-temperature NMR spectroscopy. The compounds alpha-OMe-4-cydpm and [Zn(alpha-OMe-4-mecdpm)(2)] have also been characterized by X-ray diffraction. The formation of the new dipyrrin derivatives is shown to be general and can be performed on dipyrrins with various meso-aryl substitutents, with a variety of alcohols, and can be promoted by several metal salts.
Sara R Halper; Jay R Stork; Seth M Cohen
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2007-02-08
Journal Detail:
Title:  Dalton transactions (Cambridge, England : 2003)     Volume:  -     ISSN:  1477-9226     ISO Abbreviation:  Dalton Trans     Publication Date:  2007 Mar 
Date Detail:
Created Date:  2007-02-27     Completed Date:  2007-05-08     Revised Date:  2007-12-03    
Medline Journal Info:
Nlm Unique ID:  101176026     Medline TA:  Dalton Trans     Country:  England    
Other Details:
Languages:  eng     Pagination:  1067-74     Citation Subset:  IM    
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, Calfornia 92093-0358, USA.
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MeSH Terms
Cobalt / chemistry
Crystallography, X-Ray
Indicators and Reagents
Magnetic Resonance Spectroscopy
Metals / chemistry*
Models, Molecular
Organometallic Compounds / chemical synthesis,  chemistry*
Oxidants / chemistry
Pyrroles / chemistry*
Spectrometry, Mass, Electrospray Ionization
Zinc / chemistry
Grant Support
T32 HL007444-25/HL/NHLBI NIH HHS
Reg. No./Substance:
0/Alcohols; 0/Indicators and Reagents; 0/Ligands; 0/Metals; 0/Organometallic Compounds; 0/Oxidants; 0/Pyrroles; 0/Solutions; 0/Solvents; 7440-48-4/Cobalt; 7440-66-6/Zinc

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