Thermodynamic characteristic of complex formation of some metals with 3-(4-chlorophenylazo)pentane-2,4-dione in aqueous ethanol

Alieva, R. A.; Pashaev, F. G.; Gasanov, A. G.; Mahmudov, Kamran T.

doi:10.1134/s0036023609090113

Cited by 6 publications

(7 citation statements)

References 2 publications

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“…The presence of one heterodienic system, HN-N]C-C]O, forming a fairly weak heteronuclear RAHB, N-H/O, has been supported by crystallographic data, and length of this distance N/O 2.5872(12) Å falls in the middle of the N/O distances range, 2.538-2.597 Å, as observed in previous studies on b-diketo-arylhydrazones [28]. This might be useful in the design of functional materials attributed to smart hydrogen bonding [6][7][8][9][10][11], photo-triggered structural switching [43], and targeted metal ion complexes [1][2][3][4][5][13][14][15].…”

Section: Discussionmentioning

confidence: 62%

“…All chemicals were obtained from commercial sources and were used as received. 1 H and l3 C NMR spectra were recorded on a Bruccer 300 spectrometer using tetramethylsilane as the internal reference. The infrared spectrum (4000-400 cm À1 ) was recorded on a Nicolet FT-IR Nexus spectrophotometer on KBr pellets.…”

Section: Methodsmentioning

confidence: 99%

“…Inspection of these values reveals that [38][39][40][41][42]: i The pL values decrease with increasing temperature revealing that its acidity increases with increasing temperature; ii A positive value of DH o indicates that its dissociation is accompanied by adsorption of heat and the process is endothermic; iii A large positive value of DG o indicates that the dissociation process is not spontaneous; iv A negative value of DS o is obtained due to increased order as a result of solvation processes.…”

Section: Determination Of Thermodynamic Functions Of the Dissociationmentioning

confidence: 97%

“…The coupling of aryldiazonium salts with b-dicarbonyl compounds results in the formation of a series of azoderivatives of b-diketones (ADB) that have been shown to exist as intramoleculary H-bonded arylhydrazone tautomers (Scheme 1) [1][2][3][4][5]:…”

Section: Introductionmentioning

confidence: 99%

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Quantum-chemical calculations, tautomeric, thermodynamic, spectroscopic and X-ray studies of 3-(4-fluorophenylhydrazone)pentane-2,4-dione

et al. 2010

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Section: Discussionmentioning

confidence: 62%

Section: Methodsmentioning

confidence: 99%

Section: Determination Of Thermodynamic Functions Of the Dissociationmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Quantum-chemical calculations, tautomeric, thermodynamic, spectroscopic and X-ray studies of 3-(4-fluorophenylhydrazone)pentane-2,4-dione

et al. 2010

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“…The thermodynamic parameters of the dissociation process of HL 1,2,4 were described earlier49, 60, 61 and will be considered herein for comparative purposes (Table 1). The data thus obtained testify that with the increase of temperature the acidity of HL 1–5 increases (p K decreases); hence the deprotonation is endothermic.…”

Section: Resultsmentioning

confidence: 99%

Trends in properties of para‐substituted 3‐(phenylhydrazo)pentane‐2,4‐diones

Kopylovich¹,

Mahmudov²,

Silva

et al. 2010

J of Physical Organic Chem

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Abstract:Trends between the Hammett's sigma(p) and related normal sigma(n)(p), inductive sigma(I), resonance sigma(R), negative sigma(-)(p) and positive sigma(+)(p) polar conjugation and Taft's sigma(o)(p) substituent constants and the N-H center dot center dot center dot O distance, delta(N-H) NMR chemical shift, oxidation potential (E-p/2(ox), measured in this study by cyclic voltammetry (CV)) and thermodynamic parameters (pK, Delta G(0), Delta H-0 and Delta S-0) of the dissociation process of unsubstituted 3-(phenylhydrazo)pentane-2,4-dione (HL1) and its para-substituted chloro (HL2), carboxy (HL3), fluoro (HL4) and nitro (HL5) derivatives were recognized. The best fits were found for sigma(p) and/or sigma(-)(p) in the cases of d(N center dot center dot center dot O), delta(N-H) and E-p/2(ox), showing the importance of resonance and conjugation effects in such properties, whereas for the above thermodynamic properties the inductive effects (sigma(I)) are dominant. HL2 exists in the hydrazo form in DMSO solution and in the solid state and contains an intramolecular H-bond with the N center dot center dot center dot O distance of 2.588(3)angstrom. It was also established that the dissociation process of HL1-5 is non-spontaneous, endothermic and entropically unfavourable, and that the increase in the inductive effect (sigma(I)) of para-substitutents (-H < -Cl < -COOH < -F < -NO2) leads to the corresponding growth of the N center dot center dot center dot O distance and decrease of the pK and of the changes of Gibbs free energy, of enthalpy and of entropy for the HL1-5 acid dissociation process. The electrochemical behaviour of HL1-5 was interpreted using theoretical calculations at the DFT/HF hybrid level, namely in terms of HOMO and LUMO compositions, and of reactivities induced by anodic and cathodic electron-transfers.

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