N,N'-Ethylenedi-L-cysteine (EC) and Its Metal Complexes: Synthesis, Characterization, Crystal Structures, and Equilibrium Constants.
Identifieur interne : 004363 ( Main/Exploration ); précédent : 004362; suivant : 004364N,N'-Ethylenedi-L-cysteine (EC) and Its Metal Complexes: Synthesis, Characterization, Crystal Structures, and Equilibrium Constants.
Auteurs : RBID : pubmed:11666222Abstract
N,N'-ethylenedi-L-cysteine (EC) and its indium(III) and gallium(III) complexes have been synthesized and characterized. The crystal structures of the ligand and the complexes have been determined by single-crystal X-ray diffraction. EC.2HBr.2H(2)O (C(8)H(22)Br(2)N(2)O(6)S(2)) crystallizes in the orthorhombic space group P2(1)2(1)2 with a = 12.776(3) Å, b = 13.735(2) Å, c = 5.1340 (10) Å, Z = 2, and V = 900.9(3) Å(3). The complexes Na[M(III)EC].2H(2)O (C(8)H(16)MN(2)O(6)S(2)Na) are isostructural for M = In and Ga, crystallizing in the tetragonal space group P4(2)2(1)2 with the following lattice constants for In, (Ga): a = 10.068(2) Å, (9.802(2) Å), b = 10.068(2) Å, (9.802(2) Å), c = 14.932(2) Å, (15.170(11) Å), Z = 4 (4), and V = 1513.6(5) Å(3), (1457.5(11) Å(3)). In both metal complexes, the metal atoms (In and Ga) are coordinated by six donor atoms (N(2)S(2)O(2)) in distorted octahedral coordination geometries in which two sulfur atoms and two nitrogen atoms occupy the equatorial positions, and the axial positions are occupied by two oxygen atoms of two carboxylate groups. The structures of the complexes previously predicted by molecular mechanics are compared with the crystal structures of the Ga(III) and In(III) complexes obtained experimentally. In contrast to the oxygen donors in phenolate-containing ligands, such as 1,2-ethylenebis((o-hydroxyphenyl)glycine) (EHPG) and N,N'-bis(o-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED), the thiolate donors of EC enhances affinity for In(III) relative to Ga(III). The following stability sequence has been obtained: In(III) > Ga(III) > Ni(II) > Zn(II) > Cd(II) > Pb(II) > Co(II). Evidence was also obtained for several protonated and hydroxo species of the complexes of both divalent and trivalent metals, where the corresponding protonation constants (K(MHL)) decrease with increasing stability of the chelate, ML(n)(-)(4), where M(n)()(+) represent the metal ion.
PubMed: 11666222
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">N,N'-Ethylenedi-L-cysteine (EC) and Its Metal Complexes: Synthesis, Characterization, Crystal Structures, and Equilibrium Constants.</title><author><name sortKey="Li, Yuejin" uniqKey="Li Y">Yuejin Li</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Texas A&M University, College Station, Texas 77843-3225, The Edward Mallinckrodt Institute of Radiology, Washington University School of Medicine, St. Louis, Missouri 63110, and Department of Chemistry, University of the Witwatersrand, Johannesburg, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Department of Chemistry, Texas A&M University, College Station, Texas 77843-3225, The Edward Mallinckrodt Institute of Radiology, Washington University School of Medicine, St. Louis, Missouri 63110, and Department of Chemistry, University of the Witwatersrand, Johannesburg</wicri:regionArea></affiliation></author><author><name sortKey="Martell, Arthur E" uniqKey="Martell A">Arthur E. Martell</name></author><author><name sortKey="Hancock, Robert D" uniqKey="Hancock R">Robert D. Hancock</name></author><author><name sortKey="Reibenspies, Joseph H" uniqKey="Reibenspies J">Joseph H. Reibenspies</name></author><author><name sortKey="Anderson, Carolyn J" uniqKey="Anderson C">Carolyn J. Anderson</name></author><author><name sortKey="Welch, Michael J" uniqKey="Welch M">Michael J. Welch</name></author></titleStmt><publicationStmt><date when="1996">1996</date><idno type="RBID">pubmed:11666222</idno><idno type="pmid">11666222</idno><idno type="wicri:Area/Main/Corpus">004760</idno><idno type="wicri:Area/Main/Curation">004760</idno><idno type="wicri:Area/Main/Exploration">004363</idno></publicationStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">N,N'-ethylenedi-L-cysteine (EC) and its indium(III) and gallium(III) complexes have been synthesized and characterized. The crystal structures of the ligand and the complexes have been determined by single-crystal X-ray diffraction. EC.2HBr.2H(2)O (C(8)H(22)Br(2)N(2)O(6)S(2)) crystallizes in the orthorhombic space group P2(1)2(1)2 with a = 12.776(3) Å, b = 13.735(2) Å, c = 5.1340 (10) Å, Z = 2, and V = 900.9(3) Å(3). The complexes Na[M(III)EC].2H(2)O (C(8)H(16)MN(2)O(6)S(2)Na) are isostructural for M = In and Ga, crystallizing in the tetragonal space group P4(2)2(1)2 with the following lattice constants for In, (Ga): a = 10.068(2) Å, (9.802(2) Å), b = 10.068(2) Å, (9.802(2) Å), c = 14.932(2) Å, (15.170(11) Å), Z = 4 (4), and V = 1513.6(5) Å(3), (1457.5(11) Å(3)). In both metal complexes, the metal atoms (In and Ga) are coordinated by six donor atoms (N(2)S(2)O(2)) in distorted octahedral coordination geometries in which two sulfur atoms and two nitrogen atoms occupy the equatorial positions, and the axial positions are occupied by two oxygen atoms of two carboxylate groups. The structures of the complexes previously predicted by molecular mechanics are compared with the crystal structures of the Ga(III) and In(III) complexes obtained experimentally. In contrast to the oxygen donors in phenolate-containing ligands, such as 1,2-ethylenebis((o-hydroxyphenyl)glycine) (EHPG) and N,N'-bis(o-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED), the thiolate donors of EC enhances affinity for In(III) relative to Ga(III). The following stability sequence has been obtained: In(III) > Ga(III) > Ni(II) > Zn(II) > Cd(II) > Pb(II) > Co(II). Evidence was also obtained for several protonated and hydroxo species of the complexes of both divalent and trivalent metals, where the corresponding protonation constants (K(MHL)) decrease with increasing stability of the chelate, ML(n)(-)(4), where M(n)()(+) represent the metal ion.</div></front></TEI><pubmed><MedlineCitation Status="Publisher" Owner="NLM"><PMID Version="1">11666222</PMID><DateCreated><Year>2001</Year><Month>Oct</Month><Day>22</Day></DateCreated><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1520-510X</ISSN><JournalIssue CitedMedium="Internet"><Volume>35</Volume><Issue>2</Issue><PubDate><Year>1996</Year><Month>Jan</Month><Day>17</Day></PubDate></JournalIssue><Title>Inorganic chemistry</Title><ISOAbbreviation>Inorg Chem</ISOAbbreviation></Journal><ArticleTitle>N,N'-Ethylenedi-L-cysteine (EC) and Its Metal Complexes: Synthesis, Characterization, Crystal Structures, and Equilibrium Constants.</ArticleTitle><Pagination><MedlinePgn>404-414</MedlinePgn></Pagination><Abstract><AbstractText>N,N'-ethylenedi-L-cysteine (EC) and its indium(III) and gallium(III) complexes have been synthesized and characterized. The crystal structures of the ligand and the complexes have been determined by single-crystal X-ray diffraction. EC.2HBr.2H(2)O (C(8)H(22)Br(2)N(2)O(6)S(2)) crystallizes in the orthorhombic space group P2(1)2(1)2 with a = 12.776(3) Å, b = 13.735(2) Å, c = 5.1340 (10) Å, Z = 2, and V = 900.9(3) Å(3). The complexes Na[M(III)EC].2H(2)O (C(8)H(16)MN(2)O(6)S(2)Na) are isostructural for M = In and Ga, crystallizing in the tetragonal space group P4(2)2(1)2 with the following lattice constants for In, (Ga): a = 10.068(2) Å, (9.802(2) Å), b = 10.068(2) Å, (9.802(2) Å), c = 14.932(2) Å, (15.170(11) Å), Z = 4 (4), and V = 1513.6(5) Å(3), (1457.5(11) Å(3)). In both metal complexes, the metal atoms (In and Ga) are coordinated by six donor atoms (N(2)S(2)O(2)) in distorted octahedral coordination geometries in which two sulfur atoms and two nitrogen atoms occupy the equatorial positions, and the axial positions are occupied by two oxygen atoms of two carboxylate groups. The structures of the complexes previously predicted by molecular mechanics are compared with the crystal structures of the Ga(III) and In(III) complexes obtained experimentally. In contrast to the oxygen donors in phenolate-containing ligands, such as 1,2-ethylenebis((o-hydroxyphenyl)glycine) (EHPG) and N,N'-bis(o-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED), the thiolate donors of EC enhances affinity for In(III) relative to Ga(III). The following stability sequence has been obtained: In(III) > Ga(III) > Ni(II) > Zn(II) > Cd(II) > Pb(II) > Co(II). Evidence was also obtained for several protonated and hydroxo species of the complexes of both divalent and trivalent metals, where the corresponding protonation constants (K(MHL)) decrease with increasing stability of the chelate, ML(n)(-)(4), where M(n)()(+) represent the metal ion.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Yuejin</ForeName><Initials>Y</Initials><Affiliation>Department of Chemistry, Texas A&M University, College Station, Texas 77843-3225, The Edward Mallinckrodt Institute of Radiology, Washington University School of Medicine, St. Louis, Missouri 63110, and Department of Chemistry, University of the Witwatersrand, Johannesburg, South Africa.</Affiliation></Author><Author ValidYN="Y"><LastName>Martell</LastName><ForeName>Arthur E.</ForeName><Initials>AE</Initials></Author><Author ValidYN="Y"><LastName>Hancock</LastName><ForeName>Robert D.</ForeName><Initials>RD</Initials></Author><Author ValidYN="Y"><LastName>Reibenspies</LastName><ForeName>Joseph H.</ForeName><Initials>JH</Initials></Author><Author ValidYN="Y"><LastName>Anderson</LastName><ForeName>Carolyn J.</ForeName><Initials>CJ</Initials></Author><Author ValidYN="Y"><LastName>Welch</LastName><ForeName>Michael J.</ForeName><Initials>MJ</Initials></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType>JOURNAL ARTICLE</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country></Country><MedlineTA>Inorg Chem</MedlineTA><NlmUniqueID>0366543</NlmUniqueID><ISSNLinking>0020-1669</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>1996</Year><Month>1</Month><Day>17</Day><Hour>0</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2001</Year><Month>10</Month><Day>23</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>1996</Year><Month>1</Month><Day>17</Day><Hour>0</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">11666222</ArticleId><ArticleId IdType="pii">ic941330l</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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