The Aqueous Periodate Oxidation of Aromatic and Aliphatic Carboxylic Acid Disulfides

Evans, Brian J.; Doi, Joyce Takahashi; Musker, W. Kenneth

doi:10.1080/10426509208034425

Cited by 3 publications

(3 citation statements)

References 14 publications

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“…Sonogashira coupling of 5-ethynylisophthalic acid dimethyl ester with the hydrochloride of 4-bromopyridine afforded linker IL3. IL4 was prepared from acetylation of the known 5-mercaptoisophthalic acid [24] with acetic acid anhydride. Details of the synthesis and the characterization of IL1 to IL4 and of new synthetic intermediates are given in the Experimental Section.…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR (400 MHz), 13 C{ 1 H} NMR (101 MHz) and 31 P{ 1 H}-NMR (162 MHz) spectra were measured on a Bruker AvanceIII 400 spectrometer (Bruker, Billerica, MA, USA), and 1 H-NMR (600 MHz) and 13 C{ 1 H} NMR (151 MHz) spectra on a Bruker AvanceIII 600 spectrometer (Bruker, Billerica, MA, USA). {Ru(CO)Cl(P i Pr3)2}2(1,4-(CH=CH)2-C6H4) [8], 3′,5′-dimethyl-2,2′:6′,2′′-terpyridine [22] and 5mercaptoisophthalic acid [24] were prepared according to literature methods. ESI-MS data was acquired on a Bruker micrOTOF II mass spectrometer (Bruker, Billerica, MA, USA) from partially oxidized analyte/CHCl3 solutions employing [Cp2Fe] + PF6 − as the oxidant.…”

Section: Materials and General Methodsmentioning

confidence: 99%

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Tetraruthenium Metallamacrocycles with Potentially Coordinating Appended Functionalities

et al. 2018

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We present four new tetraruthenium macrocycles built from two 1,4-divinylphenylene diruthenium and two isophthalic acid building blocks with peripheral, potentially mono- or tridentate donor functions attached to the isophthalic linkers. These macrocycles are characterized by multinuclear NMR spectroscopy, mass spectrometry and, in the case of the thioacetyl-appended complex 4, by X-ray crystallography. Cyclic and square wave voltammetry establish that the macrocycles can be oxidized in four consecutive redox steps that come as two pairs of two closely spaced one-electron waves. Spectroscopic changes observed during IR and UV/Vis/NIR spectroelectrochemical experiments (NIR = near infrared) show that the isophthalate linkers insulate the electroactive divinylphenylene diruthenium moieties against each other. The macrocycles exhibit nevertheless pronounced polyelectrochromism with highly intense absorptions in the Vis (2+/4+ states) and the NIR (2+ states) with extinction coefficients of up to >100,000 M−1·cm−1. The strong absorptivity enhancement with respect to the individual divinylphenylene diruthenium building blocks is attributed to conformational restrictions imposed by the macrocycle backbone. Moreover, the di- and tetracations of these macrocycles are paramagnetic as revealed by EPR spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Section: Materials and General Methodsmentioning

confidence: 99%

Tetraruthenium Metallamacrocycles with Potentially Coordinating Appended Functionalities

et al. 2018

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“…4,4 ‘ -Dithiobisbenzoic Acid (2). This procedure is a modified version of the procedure described by Evans for preparation of aromatic disulfides . 4-Mercaptobenzoic acid (0.53 g, 3.4 × 10 -3 mol) and iodine (0.44 g, 1.7 × 10 -3 mol) were dissolved in 10 mL of absolute ethanol.…”

Section: Methodsmentioning

confidence: 99%

Hemoglobin−Superoxide DismutaseChemical Linkages That Create a Dual-Function Protein

2005

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Chemical reagents were designed to cross-link and connect hemoglobin and superoxide dismutase, combining the oxygen transport and superoxide-removal capabilities of the red cell in a dual-function protein. Reaction of 1 with thiol-protected hemoglobin followed by reduction produces cross-linked hemoglobin with a free thiol on the cross-link. Reaction of SOD with 5 produces a cross-linked protein with a maleimide on the cross-link. Addition of the hemoglobin-thiol to the SOD-maleimide produces a protein with the desired dual properties. Hemoglobin's oxygenation cooperativity is lowered as a result of being in the conjugate, while SOD's activity is equal to that of the native protein.

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ChemInform Abstract: Aqueous Periodate Oxidation of Aromatic and Aliphatic Carboxylic Acid Disulfides.

1993

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The Aqueous Periodate Oxidation of Aromatic and Aliphatic Carboxylic Acid Disulfides

Cited by 3 publications

References 14 publications

Tetraruthenium Metallamacrocycles with Potentially Coordinating Appended Functionalities

Tetraruthenium Metallamacrocycles with Potentially Coordinating Appended Functionalities

Hemoglobin−Superoxide DismutaseChemical Linkages That Create a Dual-Function Protein

ChemInform Abstract: Aqueous Periodate Oxidation of Aromatic and Aliphatic Carboxylic Acid Disulfides.

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