A Spectrophotometric Study on <i>o</i>′-Carbomethoxy <i>p</i>-Dimethylamino-azobenzene (Me-ester of Methyl Red)

Majee, B.; Chakravarti, S. K.

doi:10.1524/zpch.1968.57.1_2.089

Cited by 4 publications

(2 citation statements)

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“…Substituents like -OH, -COOH, -NH2, -NMe2 etc. may produce large bathochromic shift of the T-T* transitions (by extending conjugation) to such an extent that the characteristic n-T* absorption is masked by this strong absorption (22). In the electronic spectrum of 5-phenylazo-8-quinolinol (Table 2), an absorption band at 380 nm and an inflexion at 450 nm indicate the azo-hydrazone tautomerism well known is such systems (23,24) and also the existence of intramolecular hydrogen bonding in the azo form (structure Ia).…”

Section: Electronic Spectramentioning

confidence: 99%

Chelated compounds and derivative of β-alkoxycarbonylalkyltin chlorides — 5-arylazo-8-quinolinolates, alizarinates, and thiocyanate: preparation and spectroscopic studies

Deb¹,

Ghosh²

1987

Can. J. Chem.

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Complex formation with chelating ligands like 5-phenylazo-8-quinolinol, 5-(21-carboxyphenylazo)-8-quinolinol, 1,2-dihydroxyanthraquinone (i.e., alizarin), and 1-nitroso-2-naphthol is due to nucleophilic attack on tin of the P-alkoxycarbonylalkyltin chlorides (a unique class of PVC stabilizer intermediates) with the subsequent elimination of h drogen chloride. A number of complexes of the types R2SnL2. RSnL2Cl, R2SnLCl, R2Sn(~'H')2, R2SnL1', and RSnLY'Cl (where R = CH30COCH2CH2-, C4H90COCH2CH2-, and CH30COCH(CH3)CH2-; LH = 5-phenylazo-8-quinolinol, l-nitroso-2-naphthol; L'HH' = 5-(21-carboxyphenylazo)-8-quinolinol; and LnH2 = 1,2-dihydroxyanthraquinone) and a thiocyanate derivative viz. (CH30COCH2CH2)2Sn(SCN)2 have been prepared. 5-Arylazo-8-quinolinols exhibit azo-hydrazone tautomeric equilibria but their complexes exist only in the azo form. P-Alkoxycarbonylethyltin alizarinates are somewhat different from other complexes. In these complexes two hydroxyl groups of alizarin have been utilised in complex formation, moreover, one of the two carbonyl groups of alizarin also remains involved in coordination to tin. In (CH30COCH2CH2)2Sn(SCN)2, the thiocyanate group is possibly linked to tin atom through nitrogen. All the complexes and the thiocyanate derivative have been characterised by elemental analyses, electronic, ir, and 'H nmr spectra. Possible structural features of the compounds are discussed.

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Section: Electronic Spectramentioning

confidence: 99%

Chelated compounds and derivative of β-alkoxycarbonylalkyltin chlorides — 5-arylazo-8-quinolinolates, alizarinates, and thiocyanate: preparation and spectroscopic studies

Deb¹,

Ghosh²

1987

Can. J. Chem.

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“…Spectrophotometric studies of the methyl-ester of methyl red (Chart 1, compound 2) exists in literature since five decades [15]. However, to the best of our knowledge, the corresponding carbon-analogue (compound 3) is non-existent in the literature.…”

Section: Introductionmentioning

confidence: 99%