Solvatochromic behaviours and structure–spectra relationships of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes

Adegoke, Olajire A.; Idowu, Olakunle S

doi:10.1016/j.saa.2009.11.045

Cited by 23 publications

(24 citation statements)

References 23 publications

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“…In addition, AZ-03 and AZ-04 possess propionic acid and butanone groups at position 7 respectively on the dye skeleton. These structural differences, despite the common functional groups have been well studied in our previous works [12,14]. In particular, the three congeners with ortho hydroxyl group exhibited azo-hydrazone tautomerism (Fig.…”

Section: Resultssupporting

confidence: 53%

“…The binding of AZ-02 thus seems to exhibit two major trends which may be explained by the ability of AZ-02 to bind to DNA as an intact molecule and its ability to ionise being a para-hydroxylated derivative. The dye has been shown from our previous studies [12] to demonstrate a Lewis acid behaviour ionising to bind to available lone pair of electrons that may be on any substrate. Since adenine, cytosine and guanine contain free amino residues, AZ-02 might be involved in hydrogen bond interactions with any or all of these bases to give the observed trends.…”

Section: Electronic Absorption Spectra Of Free Dyes and Complexesmentioning

confidence: 99%

“…The four monoazo dyes belong to the azo dye classification with structures similar to the approved colorants sunset yellow and amaranth. The various physicochemical properties of the dyes have also been documented and in particular solvatochromic assessments of the dyes proved that subtle differences exist in the behaviour of the dyes in polar and non-polar solvents principally influenced and determined by the other substituents apart from the common hydroxyl group [12]. The antimicrobial properties of these dyes, AZ-01, -02, -03 and -04 have also been studied [13].…”

Section: Introductionmentioning

confidence: 99%

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Studies of the interactions of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes with CT-DNA in aqueous medium

Adegoke

Ghosh

Jana

et al. 2012

Journal of Molecular Liquids

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Section: Resultssupporting

confidence: 53%

Section: Electronic Absorption Spectra Of Free Dyes and Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Studies of the interactions of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes with CT-DNA in aqueous medium

Adegoke

Ghosh

Jana

et al. 2012

Journal of Molecular Liquids

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“…The effects of a solvent on the absorption spectrum of a solute is an essential study for the development of solution chemistry [6][7][8][9][10][11]. When absorption spectra are measured in solvents of different properties, it is found that the positions, intensities, and shape of absorption bands are usually influenced by the solvent.…”

Section: Introductionmentioning

confidence: 99%

Spectral Study of 1,4-bis(3-(2-pyridyl)pyrazol-1-ylmethyl)benzene (PPB): UV-VIS Absorption Spectra Investigation in Single and Binary Solvents and Spectrophotometric Determination of the Dissociation Constant (pK<sub>b</sub>)

Elsherif¹,

Shuwat²,

Najar³

2016

Eurasian J Anal Chem

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The effect of solvents of different polarity and hydrogen bonding ability on electronic absorption spectra of PPB was investigated. UV absorption spectra (200-400 nm) were recorded in five single solvents and one binary solvent (DCM-EtOH). PPB has two absorption maxima (250 and 280 nm) due to pyridyl pyrazole and benzene systems. The spectral shifts and absorption maxima in various solvents were correlated with the Kamlet and Taft parameters (α, β and π*) using linear solvation energy relationships. The multiparametric analysis indicates that hydrogen bond donor ability of the solvent (for band I) and non-specific dipolar interactions of the solvents (for band II) play an important role in absorption maxima of PPB in pure solvents. Index of preferential solvation was calculated as a function of solvent composition. Preferential solvation by ethanol (band I) and by dichloromethane (band II) was detected in DCM-EtOH solvent mixture. The pKb of PPB in two solvent mixtures; EtOH -H2O & THF -H2O, were determined using UV-Vis spectrophotometry. Two graphical methods were used to estimate the base dissociation constant (pKb) using absorbance measurements. The resulting average of pKb values in the two solvent mixtures using the two methods were 10.77 and 11.14 with a standard deviation of 0.03 & 0.33, respectively.

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“…This diazonium was also utilized as a synthetic intermediate by Idowu and co-workers to create a small library of CDNBD-derived azo dyes, which were proposed as potential non-toxic azo dyes, and hence potential color additives [18,19]. The azo dyes are currently of considerable pharmaceutical and biomedical interest [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Modeling of 4-Carboxyl-2,6-dinitrobenzenediazonium Ion (CDNBD) Hydrolysis Through Addition of Water and Alkaline Buffer in a Strongly Acidic Medium

Thomas

Bioku

2015

J Solution Chem

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The transition from aryl diazonium reagent solution to a crystalline form has substantial merits, namely augmented stability and versatility. Absorbance decay data was from photometric titration with hydroxyl ion, supplied incrementally by water and alkaline buffer (pH 12.0), to 4-carboxyl-2,6-dinitrobenzenediazonium ion (CDNBD) and simpler analogs in a strongly acidic medium. The data were fitted to nested models (mono-and bi-exponential decay). Akaike's Information Criterion was used for statistical model comparison. Preferred model identification shows simpler diazonium analogs are less reactive towards hydroxyl ion when alkaline buffer solution is the diluting medium. In contrast, CDNBD hydrolysis is faster when an alkaline diluting medium is added, owing to profound positive effect of strong electron withdrawing groups on its electrophilic reactivity. Acidic diluting medium was shown, unambiguously, as a critical requirement for maintaining CDNBD, in an acidic solution as the cation species. Key input process variables were reliably predicted, using model parameters like V 1=2 and V T 1=2 , thus giving direction for optimal synthesis of crystalline CDNBD.

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Solvatochromic behaviours and structure–spectra relationships of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes

Cited by 23 publications

References 23 publications

Studies of the interactions of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes with CT-DNA in aqueous medium

Studies of the interactions of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes with CT-DNA in aqueous medium

Spectral Study of 1,4-bis(3-(2-pyridyl)pyrazol-1-ylmethyl)benzene (PPB): UV-VIS Absorption Spectra Investigation in Single and Binary Solvents and Spectrophotometric Determination of the Dissociation Constant (pK<sub>b</sub>)

Modeling of 4-Carboxyl-2,6-dinitrobenzenediazonium Ion (CDNBD) Hydrolysis Through Addition of Water and Alkaline Buffer in a Strongly Acidic Medium

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