Acid-base and metal ion-binding properties of diaminopropyl D-glucopyranoside and diaminopropyl D-mannopyranoside compounds in aqueous solution

Bin Song, Parisa Mehrkliodavandi, P. Buglyó, Yuji Mikata, Yoshie Shinohara, Kazumi Yoneda, Shigenobu Yano, Chris Orvig

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Abstract

For three sugar-appended diamine compounds (l,3-diamino-2-propyl β-o-glucopyranoside (2-β-D-Glc-pn), (25)2,3-diaminopropyl β-D-glucopyranoside (1-β-o-Glc-pn) and l,3-diamino-2-propyl a-o-mannopyranoside (2-a-DMan-pn)), acidity constants and stability constants with Ni2+, Cu2+ and Zn2+ have been measured (/= 0.16 M NaCl, 25 °C). The two acidity constants of each of the three sugar-diamines differ by 101-65 to 103'09, indicating that removal of the proton from HL+ species is more difficult than deprotonation from the fully protonated dication H2L2t. Statistical and polar effects, as well as the formation of an intramolecular hydrogen bond, may cause this increased stability of the HL+ species. The strength of the hydrogen bond and the degree of its formation (percentage) were estimated. The sugar ring has only a small influence on the intramolecular hydrogen bond formation. For the different metal ion-ligand systems, the predominating species in solution are quite different. In the Cu2+-l-β-D-Glc-pn system, the dominant species are always CuL2t and CuLf, in the pH range 4 to 10, where the total ligand concentration is larger than total metal ion concentration. For Ni2t, NiLf+ is also important under these same conditions; however, for Zn2+, the hydrolysis species ZnL2(OH)+ and ZnL2(OH)2 predominate in the high pH region. All possible species in the system were included during the calculations, and the corresponding stability constants were determined. The hydrolysis of the metal ions themselves is important in some cases and all possible hydrolysis species were included in the fitting calculation. The stability constant plots log K versus pK yielded straight reference lines for 1,3-diamine or 1,2-diamine ligands, reflecting the complete absence of sugar oxygen atoms in the metal ion coordination. The linkage between the metal ion and the diamine residue depends solely on the basicity of the ligand.

Original languageEnglish
Pages (from-to)1325-1333
Number of pages9
JournalJournal of the Chemical Society, Dalton Transactions
Issue number8
DOIs
Publication statusPublished - 2000

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Diamines
Mannose
Metal ions
Sugars
Acids
Ligands
Hydrolysis
Hydrogen bonds
Acidity
Deprotonation
Alkalinity
Protons
Oxygen
Atoms

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Acid-base and metal ion-binding properties of diaminopropyl D-glucopyranoside and diaminopropyl D-mannopyranoside compounds in aqueous solution. / Song, Bin; Mehrkliodavandi, Parisa; Buglyó, P.; Mikata, Yuji; Shinohara, Yoshie; Yoneda, Kazumi; Yano, Shigenobu; Orvig, Chris.

In: Journal of the Chemical Society, Dalton Transactions, No. 8, 2000, p. 1325-1333.

Research output: Contribution to journalArticle

Song, Bin ; Mehrkliodavandi, Parisa ; Buglyó, P. ; Mikata, Yuji ; Shinohara, Yoshie ; Yoneda, Kazumi ; Yano, Shigenobu ; Orvig, Chris. / Acid-base and metal ion-binding properties of diaminopropyl D-glucopyranoside and diaminopropyl D-mannopyranoside compounds in aqueous solution. In: Journal of the Chemical Society, Dalton Transactions. 2000 ; No. 8. pp. 1325-1333.
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abstract = "For three sugar-appended diamine compounds (l,3-diamino-2-propyl β-o-glucopyranoside (2-β-D-Glc-pn), (25)2,3-diaminopropyl β-D-glucopyranoside (1-β-o-Glc-pn) and l,3-diamino-2-propyl a-o-mannopyranoside (2-a-DMan-pn)), acidity constants and stability constants with Ni2+, Cu2+ and Zn2+ have been measured (/= 0.16 M NaCl, 25 °C). The two acidity constants of each of the three sugar-diamines differ by 101-65 to 103'09, indicating that removal of the proton from HL+ species is more difficult than deprotonation from the fully protonated dication H2L2t. Statistical and polar effects, as well as the formation of an intramolecular hydrogen bond, may cause this increased stability of the HL+ species. The strength of the hydrogen bond and the degree of its formation (percentage) were estimated. The sugar ring has only a small influence on the intramolecular hydrogen bond formation. For the different metal ion-ligand systems, the predominating species in solution are quite different. In the Cu2+-l-β-D-Glc-pn system, the dominant species are always CuL2t and CuLf, in the pH range 4 to 10, where the total ligand concentration is larger than total metal ion concentration. For Ni2t, NiLf+ is also important under these same conditions; however, for Zn2+, the hydrolysis species ZnL2(OH)+ and ZnL2(OH)2 predominate in the high pH region. All possible species in the system were included during the calculations, and the corresponding stability constants were determined. The hydrolysis of the metal ions themselves is important in some cases and all possible hydrolysis species were included in the fitting calculation. The stability constant plots log K versus pK yielded straight reference lines for 1,3-diamine or 1,2-diamine ligands, reflecting the complete absence of sugar oxygen atoms in the metal ion coordination. The linkage between the metal ion and the diamine residue depends solely on the basicity of the ligand.",
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AU - Song, Bin

AU - Mehrkliodavandi, Parisa

AU - Buglyó, P.

AU - Mikata, Yuji

AU - Shinohara, Yoshie

AU - Yoneda, Kazumi

AU - Yano, Shigenobu

AU - Orvig, Chris

PY - 2000

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AB - For three sugar-appended diamine compounds (l,3-diamino-2-propyl β-o-glucopyranoside (2-β-D-Glc-pn), (25)2,3-diaminopropyl β-D-glucopyranoside (1-β-o-Glc-pn) and l,3-diamino-2-propyl a-o-mannopyranoside (2-a-DMan-pn)), acidity constants and stability constants with Ni2+, Cu2+ and Zn2+ have been measured (/= 0.16 M NaCl, 25 °C). The two acidity constants of each of the three sugar-diamines differ by 101-65 to 103'09, indicating that removal of the proton from HL+ species is more difficult than deprotonation from the fully protonated dication H2L2t. Statistical and polar effects, as well as the formation of an intramolecular hydrogen bond, may cause this increased stability of the HL+ species. The strength of the hydrogen bond and the degree of its formation (percentage) were estimated. The sugar ring has only a small influence on the intramolecular hydrogen bond formation. For the different metal ion-ligand systems, the predominating species in solution are quite different. In the Cu2+-l-β-D-Glc-pn system, the dominant species are always CuL2t and CuLf, in the pH range 4 to 10, where the total ligand concentration is larger than total metal ion concentration. For Ni2t, NiLf+ is also important under these same conditions; however, for Zn2+, the hydrolysis species ZnL2(OH)+ and ZnL2(OH)2 predominate in the high pH region. All possible species in the system were included during the calculations, and the corresponding stability constants were determined. The hydrolysis of the metal ions themselves is important in some cases and all possible hydrolysis species were included in the fitting calculation. The stability constant plots log K versus pK yielded straight reference lines for 1,3-diamine or 1,2-diamine ligands, reflecting the complete absence of sugar oxygen atoms in the metal ion coordination. The linkage between the metal ion and the diamine residue depends solely on the basicity of the ligand.

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