Macrocyclic sulfide syntheses: A review

Bradshaw, Jerald S.; Hui, J. Y.

doi:10.1002/jhet.5570110501

Cited by 78 publications

(9 citation statements)

References 119 publications

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“…Whereas the highly electrostatic binding of the "hard" alkali and alkaline-earth cations is stronger with "hard", polar and electron rich sites, the binding of group B and transition metal cations is favoured by nitrogen and sulfur sites. Thus, whereas macrocyclic polyethers bind alkali and alkaline-earth cations [ 10-151, macrocyclic polyamines [l 11 [ 16-191 and macrocyclic polysulfides [ 111 [20] form preferentially complexes with group B and transition metal cations. Similar changes in properties should occur in the macrobicyclic topology.…”

Section: Discussionmentioning

confidence: 99%

Cryptates. XXV. Stability and selectivity of cation inclusion complexes of polyaza‐macrobicyclic ligands. Selective complexation of toxic heavy metal cations

Lehn¹,

Montavon²

1978

Helvetica Chimica Acta

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SummaryWe have measured the stability constants of the cryptate complexes formed by ligands 1-4 with alkali, alkaline-earth, transition metal and toxic heavy metal cations. Stabilities and selectivities of complexation of the alkali and alkalineearth cations are less pronounced in 1-4 than in the parent compounds 5 and 6 and decrease as the number of nitrogen sites increase. Remarkable complexation properties are found towards transition metal and toxic heavy metal cations. The intramolecular cavity of ligands 1-3 is too large for small cations like Co2+, Ni2+, Zn2+ so that the complexes formed are comparatively weak; however these cations are strongly complexed by ligand 4 whose intramolecular cavity has a much smaller size, compatible with their ionic radius. On the other hand, ligands 1-4 all form highly stable cryptates with Cd2+, Hg2+, Pb2+. Thus by the combined operation of the two structural parameters, cavity size and nature of the binding sites, cryptands 2 et 3 present very high selectivities for the complexation of these toxic heavy metal cations with respect to the biologically important ones Na+, K+, Mg2+, Ca", Zn2+. The selectivities of ligand 2 for Cd2+, Hg2+ and Pb2+ with respect to Zn2+ are as high as lo6, 10l8 and lo9 respectively. They are much more pronounced than those of previously known complexing agents. Cryptands like 2 and 3 thus present a unique selectivity sequence of special interest in detoxication (decorporation, depollution). Further structural elaboration may allow to design ligands which present a given selectivity pattern of potential use in "cryptatotherapy" and "environment pollution control". The results also provide evidence for the existence, at low pH, of protonated complexes which probably participate in an acid catalysed process for dissociation of the complexes.

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Section: Discussionmentioning

confidence: 99%

Cryptates. XXV. Stability and selectivity of cation inclusion complexes of polyaza‐macrobicyclic ligands. Selective complexation of toxic heavy metal cations

Lehn¹,

Montavon²

1978

Helvetica Chimica Acta

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“…In addition, the coordination chemistry of chelating agents with built-in thioether and azole groups (15), and macrocyclic ligands with thioether and amino, amido, pyridine, furan, and thiophene subunits, has also been explored (24)(25)(26)(27)(28)(29)(30)(31)(32)(33).…”

Section: Introductionmentioning

confidence: 99%

Coordination chemistry of thioether–pyridazine macrocycles. I. Synthetic, structural, and spectroscopic studies of Cu(II) and Cu(I) complexes of novel thioether–pyridazine macrocycles that contain two or three pyridazine subunits

Chen¹,

Thompson²,

Bridson³

1992

Can. J. Chem.

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The preparations of thioether-pyridazine macrocycles containing three (Ll) and two (L2) pyridazine subunits and their copper complexes are described. The ligands are characterized by 'H nuclear magnetic resonance and mass spectrometry and in one case by X-ray crystallography, and the complexes by infrared, electronic, and electron spin resonance (esr) spectra and in some cascs by X-ray crystallo~raphy. The compJex [ C U~( L~) ~C I~] .2CHC13 (1) crystallized in the triclinic system, space group P1 with a = 13.661(2) A, b = 14.174(3) A, c = 9.412(2) A, a = 101.08(2)", P = 96.94(2)", [Traduit par la redaction]

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“…The crystal structure of 1,2-(3'-oxapentane-I ',5'-dithiolato-SS') -1 ',2'-dicarba-closododecaborane has been determined. It crystallizes in space group P2,la with four formula units in a cell of dimensions a = 11.708 (2), b = 10.209 (3), c = 12.61 3(3) A, and p = 109.04(2)".…”

mentioning

confidence: 99%

Macrocycles incorporating closo- and nido-carbaborane cages: molecular structure of 1,2-(3′-oxapentane-1′,5′-dithiolato-SS′)-1′,2′-dicarba-closo-dodecaborane

Teixidor¹,

Romerosa²,

Rius³

et al. 1990

J. Chem. Soc., Dalton Trans.

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Macrocyclic sulfide syntheses: A review

Cited by 78 publications

References 119 publications

Cryptates. XXV. Stability and selectivity of cation inclusion complexes of polyaza‐macrobicyclic ligands. Selective complexation of toxic heavy metal cations

Cryptates. XXV. Stability and selectivity of cation inclusion complexes of polyaza‐macrobicyclic ligands. Selective complexation of toxic heavy metal cations

Coordination chemistry of thioether–pyridazine macrocycles. I. Synthetic, structural, and spectroscopic studies of Cu(II) and Cu(I) complexes of novel thioether–pyridazine macrocycles that contain two or three pyridazine subunits

Macrocycles incorporating closo- and nido-carbaborane cages: molecular structure of 1,2-(3′-oxapentane-1′,5′-dithiolato-SS′)-1′,2′-dicarba-closo-dodecaborane

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