Carbon-13 NMR and x-ray structure determination of 1-(arylazo)-2-naphthols. Intramolecular proton transfer between nitrogen and oxygen atoms in the solid state

Olivieri, Alejandro C.; Wilson, Roxy B.; Paul, Iain C.; Curtin, David Y.

doi:10.1021/ja00197a003

Cited by 133 publications

(79 citation statements)

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“…To date, only the -naphthol (1) (Jarvis, 1961;Olivieri et al, 1989;Salmen et al, 1988;Whitaker, 1977Whitaker, , 1978bGrainger & McConnell, 1969;Guggenberger & Teufer, 1975;Diamantis et al, 1992;Alcock et al, 1968), naphthol AS (2) (Kobelt et al, 1972(Kobelt et al, , 1974Whitaker, 1978a) and acetoacetanilide (3) (Paulus et al, 1983;Paulus, 1984;Gridunova et al, 1991;Paulus & Rieper, 1985;Whitaker 1983aWhitaker ,b, 1984aWhitaker ,b, 1985aWhitaker ,b,c, 1986Whitaker & Walker, 1987;Golinski, 1988) classes of pigment have given crystal structures using standard laboratory techniques. The dif®culty in growing good quality crystals is further shown by the poor quality of some of these determinations (e.g.…”

Section: Introductionmentioning

confidence: 99%

Comparison of the structural motifs of acetoacetanilides and related azo pigments

Chisholm¹,

Kennedy

Wilson³

et al. 2000

Acta Crystallogr Sect B

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The structures of three methyl-substituted acetoacetanilides and of an azo pigment derived from one of them are presented and discussed together with a review of related known crystal structures. By considering the position of any aromatic substituents it is possible to predict whether the simple acetoacetanilides adopt planar structures with intramolecular hydrogen bonding or twisted structures featuring intermolecular hydrogen bonding. However, we ®nd that the same crystal engineering rules cannot be applied to the related azo pigments: this is apparently due to the presence of an sp 2 atom which facilitates the adoption of planar conformations. The thermal properties of the acetoacetanilides were measured by DSC and are discussed with reference to their crystal structures.

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Section: Introductionmentioning

confidence: 99%

Comparison of the structural motifs of acetoacetanilides and related azo pigments

Chisholm¹,

Kennedy

Wilson³

et al. 2000

Acta Crystallogr Sect B

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“…S2 and S3 in the ESI). The phase analysis revealed that Sudan I consists of 82% of the polymorph I (Oliveri et al 1989), 8% of the polymorph II (Liu et al 1997), and 10% of the polymorph III (Ferreira et al 2013), whereas 4-methylumbelliferone exists in the anhydrous form (Panini et al 2014). …”

Section: Powder X-ray Diffractionmentioning

confidence: 99%

“…The resulted diffractograms are presented in Figs (Oliveri et al 1989), the 4-MU hydrate (Panini et al 2014), and Na 2 CO 3 ·NaHCO 3 ·2H 2 O (Candlin 1956) (see Fig. 3), whereas the base-free crystallization indicates the coexistence of crystalline forms of Sudan I, polymorph I (Oliveri et al 1989), Sudan I, polymorph II (Liu et al 1997), and 4-methylumbelliferone (Panini et al 2014). The simulated bands for Sudan I polymorph II are somewhat shifted due to temperature effect (Liu et al 1997).…”

Section: Solid-state Investigationsmentioning

confidence: 99%

Improving Fluorometric Determination of Water Content in Aprotic Solvents

et al. 2017

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A fluorometric method allowing quantification of minute amounts of water in highly lipophilic solvents is proposed. This approach takes advantage of resonance energy transfer between 4-methylumbelliferone and Sudan I. The conditions required to observe effective energy transfer have been elucidated. The emission band of the donor molecule (4-methylumbelliferone) depends strongly on the water content-its position is affected by protolytic reactions occurring between the fluorescent dye and water in lipophilic solvent media. In consequence, the extent of overlap between the emission band of the donor and absorption peak of the acceptor scales with the water concentration. The sensitivity of this optical system can be considerably increased by addition of organic bases. The dependence of the emission band of 4-methylumbelliferone/Sudan I system on minute amount of water present in lipophilic solutions opens up possibility of determination of water content in these media at the unique wavelength, in a turn on mode. The presented system was successfully applied to determine water in model commercial oil samples. It was shown that using herein proposed method the increase of water contents in the sample can be observed as increase of the emission intensity, despite the native fluorescence of the vegetable oil samples. For these samples, a good correlation with golden standard Karl Fischer titration was obtained.

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“…Azo pigments are widely used for the colouration of coatings, plastics and printing inks, with an annual sales volume of more than one billion Euros (Biswas & Umapathy, 2000). In the literature, most azo pigments are drawn with an N N double bond (Olivieri et al, 1989). However, all commercial pigments based on -naphthol adopt the hydrazone tautomeric form in the solid state, as proven by many X-ray structure determinations of -naphthol pigments.…”

Section: Structure Descriptionmentioning

confidence: 99%

(4-Aminosulfonylphenyl)[(2-oxidonaphthalen-1-yl)imino]azanium

et al. 2016

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The crystal structure of the title compound, C 16 H 13 N 3 O 3 S, shows that the two independent zwitterions in the asymmetric unit are approximately planar. Intramolecular N-HÁ Á ÁO hydrogen bonds occur and the aromatic rings have a trans configuration with respect to the azo double bond. In the crystal, the molecules are linked via N-HÁ Á ÁO hydrogen bonds and -stacking, forming a three-dimensional supramolecular network, the -stacking interactions between adjacent benzene and naphthalene rings having centroid-to-centroid distances of 3.764 (3) and 3.775 (3) Å .

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Carbon-13 NMR and x-ray structure determination of 1-(arylazo)-2-naphthols. Intramolecular proton transfer between nitrogen and oxygen atoms in the solid state

Cited by 133 publications

References 0 publications

Comparison of the structural motifs of acetoacetanilides and related azo pigments

Comparison of the structural motifs of acetoacetanilides and related azo pigments

Improving Fluorometric Determination of Water Content in Aprotic Solvents

(4-Aminosulfonylphenyl)[(2-oxidonaphthalen-1-yl)imino]azanium

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