Csanadi, Janos

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  • Csanadi, Janos (6)
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Author's Bibliography

Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode

Vajdle, Olga; Guzsvány, Valéria; Skorić, Dušan; Csanadi, Janos; Petković, Miloš; Avramov-Ivić, Milka; Kónya, Zoltán; Petrović, Slobodan; Bobrowski, Andrzej

(Pergamon-Elsevier Science Ltd, Oxford, 2017)

TY  - JOUR
AU  - Vajdle, Olga
AU  - Guzsvány, Valéria
AU  - Skorić, Dušan
AU  - Csanadi, Janos
AU  - Petković, Miloš
AU  - Avramov-Ivić, Milka
AU  - Kónya, Zoltán
AU  - Petrović, Slobodan
AU  - Bobrowski, Andrzej
PY  - 2017
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3681
AB  - The renewable silver-amalgam film electrode (Hg(Ag)FE) was applied for voltammetric characterization and determination of semi-synthetic macrolide antibiotics azithromycin (AZI), clarithromycin (CLA) and roxithromycin (ROX) in the Britton-Robinson buffer as supporting electrolyte ranging the pH from 4.0 to 11.9. All three macrolides showed reduction signals in fairly negative potential range. During direct cathodic square wave voltammetric (SWV) investigations conducted over the potential range from -0.75 V to -2.00V vs SCE, either one or two reduction peaks were obtained in the potential range from -1.5 to -1.9 V. The shapes and intensities of the signals depend on the applied pH values in wider pH ranges. For analytical purposes concerning the development of direct cathodic SWV and adsorptive stripping SWV (SW-AdSV) methods the neutral and slightly alkaline media were suitable as pH 7.2, pH 7.4 and pH 7.0 for AZI, CIA and ROX, respectively. Based on the cyclic voltammograms recorded at these pH values, adsorption-controlled electrode kinetics process can be proposed for all three macrolides. Furthermore, the water suppressed H-1 NMR measurements in the pH range between 6.0 and 10.5 indicated that the macrolide molecules at the optimal analytical conditions are predominantly in protonated form via their tertiary amino groups which supported in all three cases their adsorption on the appropriately polarized Hg(Ag)FE electrode. The optimized direct cathodic SWV methods showed good linearity in concentration ranges 4.81-23.3 mu gmL(-1), 1.96-28.6 mu gmL(-1) and 1.48-25.9 mu gmL(-1) for AZI, CIA and ROX, respectively. The development of the SW-AdSV methods resulted in the linear responses at lower concentration ranges as 1.0-2.46 mu gmL(-1), 0.05-0.99 mu gmL(-1) and 0.10-0.99 mu gmL(-1), for AZI, CIA and ROX, respectively. The relative standard deviation for all developed methods was not higher than 1.0% except the SWV method for AZI with 4.7%. In the case of all three investigated macrolide antibiotics the protonated form of the tertiary amino group(s) at appropriate accumulation potential and time favored the adsorption of the ionic form of the target molecules offering the opportunity for the development of SW-AdSV methods for their trace level analysis on Hg(Ag)FE. Optimized SW-AdSV method was applied for determination of ROX in pharmaceutical preparation Runac.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Electrochimica Acta
T1  - Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode
EP  - 344
SP  - 334
VL  - 229
DO  - 10.1016/j.electacta.2017.01.146
ER  - 
@article{
author = "Vajdle, Olga and Guzsvány, Valéria and Skorić, Dušan and Csanadi, Janos and Petković, Miloš and Avramov-Ivić, Milka and Kónya, Zoltán and Petrović, Slobodan and Bobrowski, Andrzej",
year = "2017",
abstract = "The renewable silver-amalgam film electrode (Hg(Ag)FE) was applied for voltammetric characterization and determination of semi-synthetic macrolide antibiotics azithromycin (AZI), clarithromycin (CLA) and roxithromycin (ROX) in the Britton-Robinson buffer as supporting electrolyte ranging the pH from 4.0 to 11.9. All three macrolides showed reduction signals in fairly negative potential range. During direct cathodic square wave voltammetric (SWV) investigations conducted over the potential range from -0.75 V to -2.00V vs SCE, either one or two reduction peaks were obtained in the potential range from -1.5 to -1.9 V. The shapes and intensities of the signals depend on the applied pH values in wider pH ranges. For analytical purposes concerning the development of direct cathodic SWV and adsorptive stripping SWV (SW-AdSV) methods the neutral and slightly alkaline media were suitable as pH 7.2, pH 7.4 and pH 7.0 for AZI, CIA and ROX, respectively. Based on the cyclic voltammograms recorded at these pH values, adsorption-controlled electrode kinetics process can be proposed for all three macrolides. Furthermore, the water suppressed H-1 NMR measurements in the pH range between 6.0 and 10.5 indicated that the macrolide molecules at the optimal analytical conditions are predominantly in protonated form via their tertiary amino groups which supported in all three cases their adsorption on the appropriately polarized Hg(Ag)FE electrode. The optimized direct cathodic SWV methods showed good linearity in concentration ranges 4.81-23.3 mu gmL(-1), 1.96-28.6 mu gmL(-1) and 1.48-25.9 mu gmL(-1) for AZI, CIA and ROX, respectively. The development of the SW-AdSV methods resulted in the linear responses at lower concentration ranges as 1.0-2.46 mu gmL(-1), 0.05-0.99 mu gmL(-1) and 0.10-0.99 mu gmL(-1), for AZI, CIA and ROX, respectively. The relative standard deviation for all developed methods was not higher than 1.0% except the SWV method for AZI with 4.7%. In the case of all three investigated macrolide antibiotics the protonated form of the tertiary amino group(s) at appropriate accumulation potential and time favored the adsorption of the ionic form of the target molecules offering the opportunity for the development of SW-AdSV methods for their trace level analysis on Hg(Ag)FE. Optimized SW-AdSV method was applied for determination of ROX in pharmaceutical preparation Runac.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Electrochimica Acta",
title = "Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode",
pages = "344-334",
volume = "229",
doi = "10.1016/j.electacta.2017.01.146"
}
Vajdle, O., Guzsvány, V., Skorić, D., Csanadi, J., Petković, M., Avramov-Ivić, M., Kónya, Z., Petrović, S.,& Bobrowski, A.. (2017). Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode. in Electrochimica Acta
Pergamon-Elsevier Science Ltd, Oxford., 229, 334-344.
https://doi.org/10.1016/j.electacta.2017.01.146
Vajdle O, Guzsvány V, Skorić D, Csanadi J, Petković M, Avramov-Ivić M, Kónya Z, Petrović S, Bobrowski A. Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode. in Electrochimica Acta. 2017;229:334-344.
doi:10.1016/j.electacta.2017.01.146 .
Vajdle, Olga, Guzsvány, Valéria, Skorić, Dušan, Csanadi, Janos, Petković, Miloš, Avramov-Ivić, Milka, Kónya, Zoltán, Petrović, Slobodan, Bobrowski, Andrzej, "Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode" in Electrochimica Acta, 229 (2017):334-344,
https://doi.org/10.1016/j.electacta.2017.01.146 . .
36
24
35

Voltammetric behavior of erythromycin ethylsuccinate at a renewable silver-amalgam film electrode and its determination in urine and in a pharmaceutical preparation

Vajdle, Olga; Guzsvány, Valéria; Skorić, Dušan; Anojčić, Jasmina; Jovanov, Pavle; Avramov-Ivić, Milka; Csanadi, Janos; Kónya, Zoltán; Petrović, Slobodan; Bobrowski, Andrzej

(Pergamon-Elsevier Science Ltd, Oxford, 2016)

TY  - JOUR
AU  - Vajdle, Olga
AU  - Guzsvány, Valéria
AU  - Skorić, Dušan
AU  - Anojčić, Jasmina
AU  - Jovanov, Pavle
AU  - Avramov-Ivić, Milka
AU  - Csanadi, Janos
AU  - Kónya, Zoltán
AU  - Petrović, Slobodan
AU  - Bobrowski, Andrzej
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3465
AB  - Erythromycin, a macrolide antibiotic, has similar antimicrobial spectrum to penicillin and it is widely used, especially in the treatment of patients who are allergic to penicillin. In this work, the application of a renewable silver-amalgam film electrode (Hg(Ag)FE) for the characterization and determination of erythromycin ethylsuccinate (EES), a widely used esterified form of this antibiotic, by means of cyclic voltammetry (CV) and square wave voltammetry (SWV) is presented. In the aqueous Britton-Robinson buffer (pH 5.0-9.0) that served as the supporting electrolyte, one reduction peak of EES was observed in the investigated potential range between -0.75 V and -1.80 V vs SCE, with peak potential maxima ranging from -1.59 V to -1.70 V, which strongly depended on the applied pH, as did the peak shape. For the analytical purposes the pH of 7.0 was selected, since in this electrolyte the EES peak was well-shaped and separated from the background current of the supporting electrolyte in both cases; in the direct cathodic SWV and in the case of square wave adsorptive stripping voltammetry (SW-AdSV). It was established, by the E-p-pH correlation, that protons strongly influenced the electrochemical reduction of EES. The CVs recorded between 0.025-0.50 V s (1) at pH 7.0 confirmed that the electrode reaction is adsorption-controlled. Based on the series of H-1 NMR measurements it is proved that the tertiary amino group of EES is mainly in its protonated form at pH 7.0 which may lead, at appropriate accumulation potential and time, to the favored adsorption of the target ionic form of the analyte improving on such way the sensitivity of the SW-AdSV method. The optimized procedures resulted in stable SWV responses with good linear correlation in the EES concentration range from 4.53 to 29.8 mu g mL (1) (LOD = 1.36 mu g mL (1)), and from 0.69 mu g mL (1) to 2.44 mu g mL (1) (LOD 0.21 mu g mL (1)) in the case of optimized SW-AdSV. The relative standard deviation is below 1.5%. The reliability of the elaborated procedures and thus the accuracy of the obtained results were validated by comparing them with those obtained by means of HPLC-DAD measurements. The direct cathodic SWV method was successfully applied for the determination of EES in the pharmaceutical preparation Eritromicin (R), while SW-AdSV was applied in the case of the spiked urine sample. In both cases, the standard addition method was used.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Electrochimica Acta
T1  - Voltammetric behavior of erythromycin ethylsuccinate at a renewable silver-amalgam film electrode and its determination in urine and in a pharmaceutical preparation
EP  - 54
SP  - 44
VL  - 191
DO  - 10.1016/j.electacta.2015.12.207
ER  - 
@article{
author = "Vajdle, Olga and Guzsvány, Valéria and Skorić, Dušan and Anojčić, Jasmina and Jovanov, Pavle and Avramov-Ivić, Milka and Csanadi, Janos and Kónya, Zoltán and Petrović, Slobodan and Bobrowski, Andrzej",
year = "2016",
abstract = "Erythromycin, a macrolide antibiotic, has similar antimicrobial spectrum to penicillin and it is widely used, especially in the treatment of patients who are allergic to penicillin. In this work, the application of a renewable silver-amalgam film electrode (Hg(Ag)FE) for the characterization and determination of erythromycin ethylsuccinate (EES), a widely used esterified form of this antibiotic, by means of cyclic voltammetry (CV) and square wave voltammetry (SWV) is presented. In the aqueous Britton-Robinson buffer (pH 5.0-9.0) that served as the supporting electrolyte, one reduction peak of EES was observed in the investigated potential range between -0.75 V and -1.80 V vs SCE, with peak potential maxima ranging from -1.59 V to -1.70 V, which strongly depended on the applied pH, as did the peak shape. For the analytical purposes the pH of 7.0 was selected, since in this electrolyte the EES peak was well-shaped and separated from the background current of the supporting electrolyte in both cases; in the direct cathodic SWV and in the case of square wave adsorptive stripping voltammetry (SW-AdSV). It was established, by the E-p-pH correlation, that protons strongly influenced the electrochemical reduction of EES. The CVs recorded between 0.025-0.50 V s (1) at pH 7.0 confirmed that the electrode reaction is adsorption-controlled. Based on the series of H-1 NMR measurements it is proved that the tertiary amino group of EES is mainly in its protonated form at pH 7.0 which may lead, at appropriate accumulation potential and time, to the favored adsorption of the target ionic form of the analyte improving on such way the sensitivity of the SW-AdSV method. The optimized procedures resulted in stable SWV responses with good linear correlation in the EES concentration range from 4.53 to 29.8 mu g mL (1) (LOD = 1.36 mu g mL (1)), and from 0.69 mu g mL (1) to 2.44 mu g mL (1) (LOD 0.21 mu g mL (1)) in the case of optimized SW-AdSV. The relative standard deviation is below 1.5%. The reliability of the elaborated procedures and thus the accuracy of the obtained results were validated by comparing them with those obtained by means of HPLC-DAD measurements. The direct cathodic SWV method was successfully applied for the determination of EES in the pharmaceutical preparation Eritromicin (R), while SW-AdSV was applied in the case of the spiked urine sample. In both cases, the standard addition method was used.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Electrochimica Acta",
title = "Voltammetric behavior of erythromycin ethylsuccinate at a renewable silver-amalgam film electrode and its determination in urine and in a pharmaceutical preparation",
pages = "54-44",
volume = "191",
doi = "10.1016/j.electacta.2015.12.207"
}
Vajdle, O., Guzsvány, V., Skorić, D., Anojčić, J., Jovanov, P., Avramov-Ivić, M., Csanadi, J., Kónya, Z., Petrović, S.,& Bobrowski, A.. (2016). Voltammetric behavior of erythromycin ethylsuccinate at a renewable silver-amalgam film electrode and its determination in urine and in a pharmaceutical preparation. in Electrochimica Acta
Pergamon-Elsevier Science Ltd, Oxford., 191, 44-54.
https://doi.org/10.1016/j.electacta.2015.12.207
Vajdle O, Guzsvány V, Skorić D, Anojčić J, Jovanov P, Avramov-Ivić M, Csanadi J, Kónya Z, Petrović S, Bobrowski A. Voltammetric behavior of erythromycin ethylsuccinate at a renewable silver-amalgam film electrode and its determination in urine and in a pharmaceutical preparation. in Electrochimica Acta. 2016;191:44-54.
doi:10.1016/j.electacta.2015.12.207 .
Vajdle, Olga, Guzsvány, Valéria, Skorić, Dušan, Anojčić, Jasmina, Jovanov, Pavle, Avramov-Ivić, Milka, Csanadi, Janos, Kónya, Zoltán, Petrović, Slobodan, Bobrowski, Andrzej, "Voltammetric behavior of erythromycin ethylsuccinate at a renewable silver-amalgam film electrode and its determination in urine and in a pharmaceutical preparation" in Electrochimica Acta, 191 (2016):44-54,
https://doi.org/10.1016/j.electacta.2015.12.207 . .
20
17
21

Carbon-13 substituent chemical shifts in N-1-p-substituted phenyl-5-methyl-4-carboxy uracils

Assaleh, Fathi H.; Marinković, Aleksandar; Jovanović, Bratislav Ž.; Csanadi, Janos

(Elsevier Science Bv, Amsterdam, 2007)

TY  - JOUR
AU  - Assaleh, Fathi H.
AU  - Marinković, Aleksandar
AU  - Jovanović, Bratislav Ž.
AU  - Csanadi, Janos
PY  - 2007
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1094
AB  - The C-13 NMR chemical shifts of seven N-1-p-substituted phenyl-5-methyl-4-carboxy uracils have been measured in deuterated dimethyl sulfoxide (DMSO-d sigma). The correlation analysis for the substituent-induced chemical shifts (SCS) with inductive (sigma(I)), and various resonance (sigma(R)) parameters were carried out through SSP (single substituent parameter), DSP (dual substituent parameter), and DSP-NLR (dual substituent parameter non-linear resonance) methods, as well as through multiple regression analysis. The presented calculation relative to the polar and resonance effects accounts satisfactorily for substituent effects at uracil carbon atoms. Negative rho values were found for several correlations (reverse substituent effect).
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Carbon-13 substituent chemical shifts in N-1-p-substituted phenyl-5-methyl-4-carboxy uracils
EP  - 57
IS  - 1-3
SP  - 53
VL  - 833
DO  - 10.1016/j.molstruc.2006.09.002
ER  - 
@article{
author = "Assaleh, Fathi H. and Marinković, Aleksandar and Jovanović, Bratislav Ž. and Csanadi, Janos",
year = "2007",
abstract = "The C-13 NMR chemical shifts of seven N-1-p-substituted phenyl-5-methyl-4-carboxy uracils have been measured in deuterated dimethyl sulfoxide (DMSO-d sigma). The correlation analysis for the substituent-induced chemical shifts (SCS) with inductive (sigma(I)), and various resonance (sigma(R)) parameters were carried out through SSP (single substituent parameter), DSP (dual substituent parameter), and DSP-NLR (dual substituent parameter non-linear resonance) methods, as well as through multiple regression analysis. The presented calculation relative to the polar and resonance effects accounts satisfactorily for substituent effects at uracil carbon atoms. Negative rho values were found for several correlations (reverse substituent effect).",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Carbon-13 substituent chemical shifts in N-1-p-substituted phenyl-5-methyl-4-carboxy uracils",
pages = "57-53",
number = "1-3",
volume = "833",
doi = "10.1016/j.molstruc.2006.09.002"
}
Assaleh, F. H., Marinković, A., Jovanović, B. Ž.,& Csanadi, J.. (2007). Carbon-13 substituent chemical shifts in N-1-p-substituted phenyl-5-methyl-4-carboxy uracils. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 833(1-3), 53-57.
https://doi.org/10.1016/j.molstruc.2006.09.002
Assaleh FH, Marinković A, Jovanović BŽ, Csanadi J. Carbon-13 substituent chemical shifts in N-1-p-substituted phenyl-5-methyl-4-carboxy uracils. in Journal of Molecular Structure. 2007;833(1-3):53-57.
doi:10.1016/j.molstruc.2006.09.002 .
Assaleh, Fathi H., Marinković, Aleksandar, Jovanović, Bratislav Ž., Csanadi, Janos, "Carbon-13 substituent chemical shifts in N-1-p-substituted phenyl-5-methyl-4-carboxy uracils" in Journal of Molecular Structure, 833, no. 1-3 (2007):53-57,
https://doi.org/10.1016/j.molstruc.2006.09.002 . .
10
8
9

A study of substituent effects on the NH bond in alkyl and aryl 4,6-disubstituted-3-cyano-2-pyridones

Misić-Vuković, Milica; Jovanović, Slobodanka; Mijin, Dušan; Csanadi, Janos; Đoković, Dejan

(Serbian Chemical Society, Belgrade, 2007)

TY  - JOUR
AU  - Misić-Vuković, Milica
AU  - Jovanović, Slobodanka
AU  - Mijin, Dušan
AU  - Csanadi, Janos
AU  - Đoković, Dejan
PY  - 2007
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1112
AB  - Substituent effects on the IR stretching frequencies and 1H-NMR chemical shifts of the pyridone NH group in 4- and 6-disubstituted alkyl and aryl 3-cyano- 2-pyridones were investigated. The bands most sensitive to substituent effects from the broad and multiple IR NH band for each compound were selected by a computer calculation. The selected values of the IR frequencies and the determined 1H-NMR chemical shifts were subjected to LFER analysis, by correlations with the Hamett σm/p and Swain-Lupton F and R substituent constants.
AB  - U radu je razmatran uticaj supstituenata na IR frekvencije i 1H-NMR hemijska pomeranja za piridonsku NH grupu u 4- i 6-disupstituisanim alkil i aril 3-cijano-2-piridonima korišćenjem principa linearne korelacije slobodne energije. Za izračunavanja su primenjene Hametove σm/p konstante kao i Swain-Lupton konstante supstituenata F i R. Razvijen je kompjuterski metod za izbor IR NH traka najosetljivijih na uticaj supstituenata.
PB  - Serbian Chemical Society, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - A study of substituent effects on the NH bond in alkyl and aryl 4,6-disubstituted-3-cyano-2-pyridones
T1  - Korelaciona analiza IR i 1H-NMR spektralnih podataka za NH vezu u alkil i aril 4,6-disupstituisanim 3-cijano-2-piridonima
EP  - 1236
IS  - 12
SP  - 1229
VL  - 72
UR  - https://hdl.handle.net/21.15107/rcub_technorep_1112
ER  - 
@article{
author = "Misić-Vuković, Milica and Jovanović, Slobodanka and Mijin, Dušan and Csanadi, Janos and Đoković, Dejan",
year = "2007",
abstract = "Substituent effects on the IR stretching frequencies and 1H-NMR chemical shifts of the pyridone NH group in 4- and 6-disubstituted alkyl and aryl 3-cyano- 2-pyridones were investigated. The bands most sensitive to substituent effects from the broad and multiple IR NH band for each compound were selected by a computer calculation. The selected values of the IR frequencies and the determined 1H-NMR chemical shifts were subjected to LFER analysis, by correlations with the Hamett σm/p and Swain-Lupton F and R substituent constants., U radu je razmatran uticaj supstituenata na IR frekvencije i 1H-NMR hemijska pomeranja za piridonsku NH grupu u 4- i 6-disupstituisanim alkil i aril 3-cijano-2-piridonima korišćenjem principa linearne korelacije slobodne energije. Za izračunavanja su primenjene Hametove σm/p konstante kao i Swain-Lupton konstante supstituenata F i R. Razvijen je kompjuterski metod za izbor IR NH traka najosetljivijih na uticaj supstituenata.",
publisher = "Serbian Chemical Society, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "A study of substituent effects on the NH bond in alkyl and aryl 4,6-disubstituted-3-cyano-2-pyridones, Korelaciona analiza IR i 1H-NMR spektralnih podataka za NH vezu u alkil i aril 4,6-disupstituisanim 3-cijano-2-piridonima",
pages = "1236-1229",
number = "12",
volume = "72",
url = "https://hdl.handle.net/21.15107/rcub_technorep_1112"
}
Misić-Vuković, M., Jovanović, S., Mijin, D., Csanadi, J.,& Đoković, D.. (2007). A study of substituent effects on the NH bond in alkyl and aryl 4,6-disubstituted-3-cyano-2-pyridones. in Journal of the Serbian Chemical Society
Serbian Chemical Society, Belgrade., 72(12), 1229-1236.
https://hdl.handle.net/21.15107/rcub_technorep_1112
Misić-Vuković M, Jovanović S, Mijin D, Csanadi J, Đoković D. A study of substituent effects on the NH bond in alkyl and aryl 4,6-disubstituted-3-cyano-2-pyridones. in Journal of the Serbian Chemical Society. 2007;72(12):1229-1236.
https://hdl.handle.net/21.15107/rcub_technorep_1112 .
Misić-Vuković, Milica, Jovanović, Slobodanka, Mijin, Dušan, Csanadi, Janos, Đoković, Dejan, "A study of substituent effects on the NH bond in alkyl and aryl 4,6-disubstituted-3-cyano-2-pyridones" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1229-1236,
https://hdl.handle.net/21.15107/rcub_technorep_1112 .
3
5

Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(substituted phenylmethylene)-3-and-4-aminobenzoic acids

Jovanović, Bratislav Ž.; Marinković, Aleksandar; Assaleh, Fathi H.; Csanadi, Janos

(Elsevier Science Bv, Amsterdam, 2005)

TY  - JOUR
AU  - Jovanović, Bratislav Ž.
AU  - Marinković, Aleksandar
AU  - Assaleh, Fathi H.
AU  - Csanadi, Janos
PY  - 2005
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/822
AB  - C-13 chemical shifts of the azomethine carbon atom for N-(substituted phenylmethylene)-3- and -4-aminobenzoic acids having a wide range of substituent effects, were determined in deuterated DMSO solution. Good Hammett correlations of the C-13 NMR chemical shifts of azomethine carbons with electrophilic substituent constants sigma(+)(p) for electron-donor substituents for both series of acids indicate an important resonance interaction of the substituents on the benzylidene ring with the azomethine carbon atom. On the other hand, good correlations of the 13 C NMR chemical shifts of azomethine carbon atom of both series of acids with inductive substituent constants for electron-acceptor substituents in benzylidene ring indicates that the chemical shifts are influenced only by inductive effect of the substituents. The demand for electrons by the azomethine carbon atom in both investigated series have been compared, discussing the mode of transmission of substituent effects, both inductive and resonance, in relation to the geometry of investigated imines.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(substituted phenylmethylene)-3-and-4-aminobenzoic acids
EP  - 416
SP  - 411
VL  - 744
DO  - 10.1016/j.molstruc.2004.12.028
ER  - 
@article{
author = "Jovanović, Bratislav Ž. and Marinković, Aleksandar and Assaleh, Fathi H. and Csanadi, Janos",
year = "2005",
abstract = "C-13 chemical shifts of the azomethine carbon atom for N-(substituted phenylmethylene)-3- and -4-aminobenzoic acids having a wide range of substituent effects, were determined in deuterated DMSO solution. Good Hammett correlations of the C-13 NMR chemical shifts of azomethine carbons with electrophilic substituent constants sigma(+)(p) for electron-donor substituents for both series of acids indicate an important resonance interaction of the substituents on the benzylidene ring with the azomethine carbon atom. On the other hand, good correlations of the 13 C NMR chemical shifts of azomethine carbon atom of both series of acids with inductive substituent constants for electron-acceptor substituents in benzylidene ring indicates that the chemical shifts are influenced only by inductive effect of the substituents. The demand for electrons by the azomethine carbon atom in both investigated series have been compared, discussing the mode of transmission of substituent effects, both inductive and resonance, in relation to the geometry of investigated imines.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(substituted phenylmethylene)-3-and-4-aminobenzoic acids",
pages = "416-411",
volume = "744",
doi = "10.1016/j.molstruc.2004.12.028"
}
Jovanović, B. Ž., Marinković, A., Assaleh, F. H.,& Csanadi, J.. (2005). Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(substituted phenylmethylene)-3-and-4-aminobenzoic acids. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 744, 411-416.
https://doi.org/10.1016/j.molstruc.2004.12.028
Jovanović BŽ, Marinković A, Assaleh FH, Csanadi J. Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(substituted phenylmethylene)-3-and-4-aminobenzoic acids. in Journal of Molecular Structure. 2005;744:411-416.
doi:10.1016/j.molstruc.2004.12.028 .
Jovanović, Bratislav Ž., Marinković, Aleksandar, Assaleh, Fathi H., Csanadi, Janos, "Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(substituted phenylmethylene)-3-and-4-aminobenzoic acids" in Journal of Molecular Structure, 744 (2005):411-416,
https://doi.org/10.1016/j.molstruc.2004.12.028 . .
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C-13 NMR spectra of pyridine chalcone analogs

Jovanović, Bratislav Ž.; Misić-Vuković, Milica; Marinković, Aleksandar; Csanadi, Janos

(Elsevier, Amsterdam, 1999)

TY  - JOUR
AU  - Jovanović, Bratislav Ž.
AU  - Misić-Vuković, Milica
AU  - Marinković, Aleksandar
AU  - Csanadi, Janos
PY  - 1999
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/238
AB  - C-13 NMR spectra of two series of pyridine chalcone analogs were determined in deuterated dimethylsulphoxide (DMSO-d(6)). It was established that these compounds were in more stable E-configurations except for the 4-pyridalacetophenone which was in Z-configuration. On the basis of the Hammett correlations of C-13 NMR chemical shifts of the ethylenic bond carbon atoms and the a values for the pyridine "aza" groups, the polarization of ethylenic bonds were discussed. It was established that the opposite effect of the pyridine substituents at the electronic density distribution in pyridalacetophenone and cinnamoylpyridines depends on its direct bonding to the ethylenic carbon or the transmission electronic effects via the carbonyl group, respectively.
PB  - Elsevier, Amsterdam
T2  - Journal of Molecular Structure
T1  - C-13 NMR spectra of pyridine chalcone analogs
EP  - 374
SP  - 371
VL  - 482
DO  - 10.1016/S0022-2860(98)00859-X
ER  - 
@article{
author = "Jovanović, Bratislav Ž. and Misić-Vuković, Milica and Marinković, Aleksandar and Csanadi, Janos",
year = "1999",
abstract = "C-13 NMR spectra of two series of pyridine chalcone analogs were determined in deuterated dimethylsulphoxide (DMSO-d(6)). It was established that these compounds were in more stable E-configurations except for the 4-pyridalacetophenone which was in Z-configuration. On the basis of the Hammett correlations of C-13 NMR chemical shifts of the ethylenic bond carbon atoms and the a values for the pyridine "aza" groups, the polarization of ethylenic bonds were discussed. It was established that the opposite effect of the pyridine substituents at the electronic density distribution in pyridalacetophenone and cinnamoylpyridines depends on its direct bonding to the ethylenic carbon or the transmission electronic effects via the carbonyl group, respectively.",
publisher = "Elsevier, Amsterdam",
journal = "Journal of Molecular Structure",
title = "C-13 NMR spectra of pyridine chalcone analogs",
pages = "374-371",
volume = "482",
doi = "10.1016/S0022-2860(98)00859-X"
}
Jovanović, B. Ž., Misić-Vuković, M., Marinković, A.,& Csanadi, J.. (1999). C-13 NMR spectra of pyridine chalcone analogs. in Journal of Molecular Structure
Elsevier, Amsterdam., 482, 371-374.
https://doi.org/10.1016/S0022-2860(98)00859-X
Jovanović BŽ, Misić-Vuković M, Marinković A, Csanadi J. C-13 NMR spectra of pyridine chalcone analogs. in Journal of Molecular Structure. 1999;482:371-374.
doi:10.1016/S0022-2860(98)00859-X .
Jovanović, Bratislav Ž., Misić-Vuković, Milica, Marinković, Aleksandar, Csanadi, Janos, "C-13 NMR spectra of pyridine chalcone analogs" in Journal of Molecular Structure, 482 (1999):371-374,
https://doi.org/10.1016/S0022-2860(98)00859-X . .
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