Synthesis and characterization of some reversible iron(II) dioxygen carriers of lacunar macrobicyclic ligands and their reactivities with dioxygen

Herron, Norman; Zimmer, L. Lawrence; Grzybowski, Joseph J.; Olszanski, Dennis J.; Jackels, Susan C.; Callahan, Robert W.; Cameron, John A.; Christoph, Gary G.; Busch, Daryle H.

doi:10.1021/ja00360a008

Cited by 41 publications

(18 citation statements)

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“…Influence of Temperature and Pressure on the Kinetics of Reaction of Fe II L with CO. The complex [Fe II (PhBzXy)](PF 6 ) 2 exists in solution (acetonitrile) as a five-coordinate species . Iron is surrounded by four nitrogen donors from the macrocycle in the equatorial positions.…”

Section: Resultsmentioning

confidence: 99%

“…Iron(II) cyclidene compounds (Figure ) are non-porphyrin complexes that have received considerable attention as functional mimics for naturally occurring heme proteins. The binding reactions of small ligands, such as dioxygen and carbon monoxide, have been studied extensively. , A systematic investigation of the reactions of the series of iron(II) cyclidenes with carbon monoxide was performed in order to elucidate the dependence of the kinetic and dynamic parameters on the structural features of these versatile compounds. Macrocycle ligand substituents were found to have large effects on binding and dissociative rate constants, and steric interactions were found to dominate the observed effects.…”

Section: Introductionmentioning

confidence: 99%

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Mechanistic Insight from Energy and Volume Profiles for CO Binding to a Lacunar Iron(II) Cyclidene Complex

1998

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The binding of CO to a lacunar Fe(II) cyclidene complex is characterized by very negative values for the activation entropy and activation volume, whereas the reverse dissociation reaction is accompanied by small positive activation entropy and activation volume data. The constructed volume profile suggests that, in the transition state, CO disappears completely into the ligand pocket during partial Fe−CO bond formation, followed by a high-spin to low-spin transition on Fe(II) during which the metal center moves into the ligand plane and accounts for the subsequent volume decrease.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mechanistic Insight from Energy and Volume Profiles for CO Binding to a Lacunar Iron(II) Cyclidene Complex

1998

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“…The family of tetraaza macrocycles first reported by Jäger 1 displays a fascinating interplay of structure-reactivity relationships and this has been exploited to interesting effect, in particular by Busch and Cairns, in the production of the socalled 'cyclidene' macrocyclic complexes 2 where examples have been used in reversible oxygen binding, 3 as models for cytochrome P-450, 4 and in supramolecular chemistry. 5 The solid state structure of the Jäger macrocycles varies widely with ring size.…”

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First example of a sixteen membered Jäger macrocycle having a ‘Z’ conformation

Cameron¹,

Nicol²,

Rosair³

1998

Chem. Commun.

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“…The square pyramidal geometry around Fe(II) is built from three unidentate and one bidentate ligand /43b/, one unidentate and one tetradentate ligand [134][135][136][137][138][139][140][141][142][143][144][145][146][147][148][149]153,156/, one unidentate and two bidentate ligands /150-152/ and one bidentate and one tridentate set of ligands /154,155/. The square pyramidal geometry around Fe(II) is built from three unidentate and one bidentate ligand /43b/, one unidentate and one tetradentate ligand [134][135][136][137][138][139][140][141][142][143][144][145][146][147][148][149]153,156/, one unidentate and two bidentate ligands /150-152/ and one bidentate and one tridentate set of ligands /154,155/.…”

Section: Reviews In Inorganic Chemistrymentioning

confidence: 99%

Structural Aspects of Iron Coordination Compounds: I. Monomeric Derivatives

Melnı́k¹,

Ondrejkovičová²,

Vancovd³

et al. 1997

Reviews in Inorganic Chemistry

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This review summarises almost nine hundred crystallographic structures of monomelic iron coordination compounds. The number of examples per given oxidation state for the iron increases in the order: Fe(-II) (tetrahedral) < Fe(-I) (tetrahedral) < Fe(IV) (six coordinated and square pyramidal) < Fe(0) (five coordinated ) < Fe(I) (square pyramidal and square planar) < Fe(III) (three -to seven coordinated) < Fe(II) (two -to eight and ten coordinated). Variations and trends in bond lengths and angles are discussed. CeHieNeSa bis(S-methylisothiosemicarbazone)2,4-pentanedionate (2-) C9H21N3O9P3 trianion of N,N',N"-tris(dioxophosphorylmethyl)-l,4,7triazacyclononane Ci oH] 2 S 8 tetra(methylthio)tetrathiafulvalenium( 1+) Ci 4H20O 4-tert-butyl-2,6-dimethylacetophenone Ci 4N32N6 1,2-bis( 1,4,7-triaza -1 -cyclononyl)ethane Ci 5H110 2 1,3-diphenyl-l ,3 -propanedionate( 1 -) C15H23N5 2,13 -dimethyl-3,6,9,12,18pentaazabicyclo[12.3.1]octadeca-l(18),2,12,14,16pentaene Ci 5H23S 2,4,6-triisopropylbenzenethiolate( 1 -) Q5H27N5 2,13 -dimethyl-3,6,9,12,18pentaazabicyclo[12.3.1]octadeca(18),14,16-triene C16H13N3O2S dianion of S-methyl-N' ^-bisCsalicylidene) isothiosemicarbazide C16H25N5 2,14-dimethyl -3,6,10,13,19 -pentaazabicyclo [13.3.1] nonadeca-l(19),2,13,15,17-pentaene C16H32N4 5,7,7,12,14,14-hexamethyl-l,4,8,11-tetraazacyclotetra deca-4,11-diene Ci 7H17N5 bis(benzimidazol-2-ylmethyl)methylamine Ci 8 H] 8 N 6 conjugated 14-membered ring of hexaaza ligand C20H14N2O2 2,2'-[o-phenylenebis(nitrilomethylidine)diphenolate-N,N',0,0'(2-) C20H24N2O2 N-n-propylsalicylaldiminate (2-) C21H19N7 cation derived from 1,10-phenanthroline and 2,6pyridine dicarbonyls C22H22N2O2 l,l'-diphenyl-3,3'-(ethylenediimino)di-l-butanonate (2-) C22H20N2O4S dianion of Ν,Ν'-(1,3 -dimethyl-1,3 -diphenyl-2-thiapropyl)-2,3-dihydroxyterephthalic acid amide C22H22N4 7,16-dihydro-6,8,15,17-tetramethyldibenzo[fc,/] [1,4,8,1 l]tetraazacyclotetradecanate (2-) C22H25O6 atrovenetin orange trimethyl ether C22H34N4O5 macrocyclic tetraamide C23H21N7 quinquedentate macrocyclic ligand C23H25N7O2 6,13 -(bis-2-hydroxyethyl)-6H, 13H-tripyrido[cd,fg,lm] -[1,2,4,7,9,10,13] heptaaza-pentadecine C24H36N12 1,4,7,10-tetrakis(pyrazol-l-ylmethyl)-l,4,7,10tetraazacyclododecane 59

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Synthesis and characterization of some reversible iron(II) dioxygen carriers of lacunar macrobicyclic ligands and their reactivities with dioxygen

Cited by 41 publications

References 1 publication

Mechanistic Insight from Energy and Volume Profiles for CO Binding to a Lacunar Iron(II) Cyclidene Complex

Mechanistic Insight from Energy and Volume Profiles for CO Binding to a Lacunar Iron(II) Cyclidene Complex

First example of a sixteen membered Jäger macrocycle having a ‘Z’ conformation

Structural Aspects of Iron Coordination Compounds: I. Monomeric Derivatives

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