Solvatochromism of Heteroaromatic Compounds: XXIII. Reversible Specific Solvatochromic Effect in the IR Spectra of 2-Nitrophenol and 2,4,6-Trinitrophenol

Вокин, А. И.; Gavrilova, G. M.; Шулунова, А. М.; Krivoruchka, I. G.; Aksamentova, T. N.; Turchaninov, V. K.

doi:10.1023/b:rugc.0000025510.90789.3c

Cited by 7 publications

(6 citation statements)

References 18 publications

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“…Moreover, on dissolution of phenol IV in acetonitrile we observed disappearance of the lowfrequency band (w t , cm 31 : cyclohexane 432; Here m, s a , b, and e are constants characteristic of a given indicator and n 0 OH is the OH stretching vibration frequency of the molecule under conditions of nonspecific solvation with an aprotic protophilic medium. Previously such equation was applied to success for description of the solvatochromism of the n OH band of picric acid [2].…”

Section: State Of Intramolecular Ohbr Bond In Solvation Complexesmentioning

confidence: 99%

“…The resulting data allowed us to use the entire set of aprotic protophilic solvents for analysis, which much extended the range of variation of the b parameter and thus served for a more reliable description of the solvatochromism. Equations (8) and (9) are linear in parameters, which distinguishes them from the corresponding equations for H-complexes with a bifurcate (threecenter) hydrogen bond [2,35]. Comparison of the regression coefficients s a at the parameter p * in Eqs.…”

Section: Molecular Structure and Formation Energy Of Salvation H-compmentioning

confidence: 99%

“…This configuration is attained by deformation of the bond angle of the phenolic hydroxy group. Such structural reorganization is very important to take into account in considering spectroscopic effects of bifurcate hydrogen bonds containing an intramolecular component [2].…”

Section: Molecular Structure and Formation Energy Of Salvation H-compmentioning

confidence: 99%

“…In view of the fact that quantumchemical calculations of the dipole moments of benzene complexes take account of pair interactions only (microscopic level), and the dipole moments in solutions depend on two types of solvation (specific and nonspecific), we had to decide which macroscopic properties affect the dipole moment. To this end, we made use of model compounds whose solvation by benzene occurs by the nonspecific mechanism exclusively [4-nitrobenzenesulfonyl chloride (XXII), 2,5-dinitroanisole (XXIII), 2,4,6-trinitroanisole [2]. b Experimental data [37,38].…”

Section: Molecular Structure and Formation Energy Of Salvation H-compmentioning

confidence: 99%

“…In work [2], based on a phenomenological notion of complexes with a bifurcate (three-center) hydrogen bond comprising both an intra-and an intermolecular components, has predicted the effect of the formation energy of such complexes on their n XH vibration frequency. For compounds with a weak intramolecular hydrogen bond, two possibilities have been predicted: a monotonic nonlinear or nearly linear dependence of n XH on the H-bond affinity the subunit of the complex.…”

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Solvatochromism of Heteroaromatic Compounds: XXV. Effect of Bifurcate Hydrogen Bond with a Weak Intramolecular Component on the IR, NMR, and UV Spectra of 2,6-Dibromo-4-nitrophenol

et al. 2005

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Dissolution of 2,6-dibromo-4-nitrophenol in aprotic protophilic solvents forms a three-center solvation H-complex with a sharply weakened intramolecular hydrogen bond. This weakening is associated with a deformation of the bond angle of the hydroxy group. It is only on interaction with weak p-bases that the intramolecular component of the bifurcate hydrogen bond appreciably affects the spectral position of the OH stretching vibration band; this results in a nonlinear dependence between vOH and the Kamlet3Taft solvatochromic parameter.In work [2], based on a phenomenological notion of complexes with a bifurcate (three-center) hydrogen bond comprising both an intra-and an intermolecular components, has predicted the effect of the formation energy of such complexes on their n XH vibration frequency. For compounds with a weak intramolecular hydrogen bond, two possibilities have been predicted: a monotonic nonlinear or nearly linear dependence of n XH on the H-bond affinity the subunit of the complex.To test this hypothesis, in the present work we have studied 2,6-dibromo-4-nitrophenol, a compound with a weak intramolecular OH...Br bond [3315], by means of IR, NMR, and UV spectroscopy and quantum chemistry.

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Section: State Of Intramolecular Ohbr Bond In Solvation Complexesmentioning

confidence: 99%

Section: Molecular Structure and Formation Energy Of Salvation H-compmentioning

confidence: 99%

Section: Molecular Structure and Formation Energy Of Salvation H-compmentioning

confidence: 99%

Section: Molecular Structure and Formation Energy Of Salvation H-compmentioning

confidence: 99%

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Solvatochromism of Heteroaromatic Compounds: XXV. Effect of Bifurcate Hydrogen Bond with a Weak Intramolecular Component on the IR, NMR, and UV Spectra of 2,6-Dibromo-4-nitrophenol

et al. 2005

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1H and 13C NMR Study of Bifurcated Intramolecular Hydrogen Bonds in 2,6-Bis(2-pyrrolyl)pyridine and 2,6-Bis(1-vinyl-2-pyrrolyl)pyridine

et al. 2005

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According to the 1 H and 13 C NMR data, bifurcated intramolecular hydrogen bond NH···N··· HN in 2,6-bis(2-pyrrolyl)pyridine fixes its molecule in a conformation with syn orientation of the pyrrole rings. An analogous bifurcated hydrogen bond CH · · · N · · · HC is formed in 2,6-bis(1-vinyl-2-pyrrolyl)pyridine. 2-(1-Vinyl-2-pyrrolyl)-6-(2-pyrrolyl)pyridine is characterized by unsymmetrical bifurcated hydrogen bond NH···N···HC.Systematic studies on the 1 H and 13 C NMR spectra of a wide series of pyrrole derivatives [1-7] allowed us to distinguish 2-hetarylpyrroles as a class of compounds giving rise to various intramolecular hydrogen bonds. For example, a weak intramolecular hydrogen bond CH · · · N between the -hydrogen atom of the vinyl group and pyridine nitrogen atom was found in 1-vinyl-2-(2-pyridyl)pyrrole [6]. 2-(2-Pyridyl)pyrrole is characterized by a weak intramolecular hydrogen bond NH···N between the pyrrole N-H atom and pyridine nitrogen atom [4]. The 1 H NMR and IR spectra of 5-(2-pyridyl)-2-trifluoroacetylpyrrole revealed a bifurcated hydrogen bond involving both pyridine nitrogen atom and carbonyl oxygen atom of the trifluoroacetyl group [4,5]. In continuation of our studies on intramolecular hydrogen bonds in pyrrole derivatives, in the present work we examined the 1 H and 13 C NMR spectra of 2,6-bis(2-pyrrolyl)pyridine (I) and 2,6-bis-(1-vinyl-2-pyrrolyl)pyridine (VI) and compared the results with those found for model compounds II-V and VII-XIV.The 1 H and 13 C NMR spectra of pyrroles I-XIV are given in Tables 1 and 2, and the 13 C-1 H coupling constants are collected in Table 3. Following the previously used algorithm for studying 2-hetarylpyrroles by NMR spectroscopy, let us consider first the character of , conjugation between the heterorings in compounds I and VI on the basis of the corresponding carbon chemical shifts. We showed in [4] that the signals from C 3' and C 5' in the pyridine ring of I-V, R 1 = H; I, R 2 = H; II, R 2 = 2-pyridyl; III, R 2 = 3-pyridyl; IV, R 2 = 4-pyridyl; V, R 2 = Ph; VI-XIII, R 1 = CH 2 =CH; VI, VII, R 2 = CH 2 =CH; VIII, R 2 = 2-pyridyl; IX, R 2 = 3-pyridyl; X, R 2 = 4-pyridyl; XI, R 2 = Ph; XII, XIII, R 2 = H. 3'2'

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2-nitro-4-nonylphenol-based extractant for selective extraction of lithium from carbonate precipitation mother liquors

Bezdomnikov,

Sharov,

Kostikova

et al. 2024

Journal of Water Process Engineering

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Solvatochromism of Heteroaromatic Compounds: XXIII. Reversible Specific Solvatochromic Effect in the IR Spectra of 2-Nitrophenol and 2,4,6-Trinitrophenol

Cited by 7 publications

References 18 publications

Solvatochromism of Heteroaromatic Compounds: XXV. Effect of Bifurcate Hydrogen Bond with a Weak Intramolecular Component on the IR, NMR, and UV Spectra of 2,6-Dibromo-4-nitrophenol

Solvatochromism of Heteroaromatic Compounds: XXV. Effect of Bifurcate Hydrogen Bond with a Weak Intramolecular Component on the IR, NMR, and UV Spectra of 2,6-Dibromo-4-nitrophenol

1H and 13C NMR Study of Bifurcated Intramolecular Hydrogen Bonds in 2,6-Bis(2-pyrrolyl)pyridine and 2,6-Bis(1-vinyl-2-pyrrolyl)pyridine

2-nitro-4-nonylphenol-based extractant for selective extraction of lithium from carbonate precipitation mother liquors

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