Csanadi, Janos

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  • Csanadi, Janos (4)
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Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode

Vajdle, Olga; Guzsvány, Valéria; Škorić, Dušan; Csanadi, Janos; Petkovic, Milos; Avramov Ivić, Milka; Kónya, Zoltán; Petrović, Slobodan D.; Bobrowski, Andrzej

(Oxford : Pergamon-Elsevier Science Ltd, 2017)

TY  - JOUR
AU  - Vajdle, Olga
AU  - Guzsvány, Valéria
AU  - Škorić, Dušan
AU  - Csanadi, Janos
AU  - Petkovic, Milos
AU  - Avramov Ivić, Milka
AU  - Kónya, Zoltán
AU  - Petrović, Slobodan D.
AU  - Bobrowski, Andrzej
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2187
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  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Electrochimica Acta
T1  - Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode
VL  - 229
SP  - 334
EP  - 344
DO  - 10.1016/j.electacta.2017.01.146
ER  - 
@article{
author = "Vajdle, Olga and Guzsvány, Valéria and Škorić, Dušan and Csanadi, Janos and Petkovic, Milos and Avramov Ivić, Milka and Kónya, Zoltán and Petrović, Slobodan D. 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 = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Electrochimica Acta",
title = "Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver - amalgam film electrode",
volume = "229",
pages = "334-344",
doi = "10.1016/j.electacta.2017.01.146"
}
Vajdle, O., Guzsvány, V., Škorić, D., Csanadi, J., Petkovic, M., Avramov Ivić, M., Kónya, Z., Petrović, S. D.,& 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
Oxford : Pergamon-Elsevier Science Ltd., 229, 334-344.
https://doi.org/10.1016/j.electacta.2017.01.146
Vajdle O, Guzsvány V, Škorić D, Csanadi J, Petkovic M, Avramov Ivić M, Kónya Z, Petrović SD, 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, Škorić, Dušan, Csanadi, Janos, Petkovic, Milos, Avramov Ivić, Milka, Kónya, Zoltán, Petrović, Slobodan D., 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
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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; Škorić, Dušan; Anojčić, Jasmina; Jovanov, Pavle; Avramov Ivić, Milka; Csanadi, Janos; Kónya, Zoltán; Petrović, Slobodan D.; Bobrowski, Andrzej

(Oxford : Pergamon-Elsevier Science Ltd, 2016)

TY  - JOUR
AU  - Vajdle, Olga
AU  - Guzsvány, Valéria
AU  - Škorić, Dušan
AU  - Anojčić, Jasmina
AU  - Jovanov, Pavle
AU  - Avramov Ivić, Milka
AU  - Csanadi, Janos
AU  - Kónya, Zoltán
AU  - Petrović, Slobodan D.
AU  - Bobrowski, Andrzej
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4319
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  - Oxford : Pergamon-Elsevier Science Ltd
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
VL  - 191
SP  - 44
EP  - 54
DO  - 10.1016/j.electacta.2015.12.207
ER  - 
@article{
author = "Vajdle, Olga and Guzsvány, Valéria and Škorić, Dušan and Anojčić, Jasmina and Jovanov, Pavle and Avramov Ivić, Milka and Csanadi, Janos and Kónya, Zoltán and Petrović, Slobodan D. 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 = "Oxford : Pergamon-Elsevier Science Ltd",
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",
volume = "191",
pages = "44-54",
doi = "10.1016/j.electacta.2015.12.207"
}
Vajdle, O., Guzsvány, V., Škorić, D., Anojčić, J., Jovanov, P., Avramov Ivić, M., Csanadi, J., Kónya, Z., Petrović, S. D.,& 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
Oxford : Pergamon-Elsevier Science Ltd., 191, 44-54.
https://doi.org/10.1016/j.electacta.2015.12.207
Vajdle O, Guzsvány V, Škorić D, Anojčić J, Jovanov P, Avramov Ivić M, Csanadi J, Kónya Z, Petrović SD, 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, Škorić, Dušan, Anojčić, Jasmina, Jovanov, Pavle, Avramov Ivić, Milka, Csanadi, Janos, Kónya, Zoltán, Petrović, Slobodan D., 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

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; Škorić, Dušan; Anojčić, Jasmina; Jovanov, Pavle; Avramov Ivić, Milka; Csanadi, Janos; Kónya, Zoltán; Petrović, Slobodan D.; Bobrowski, Andrzej

(Oxford : Pergamon-Elsevier Science Ltd, 2016)

TY  - JOUR
AU  - Vajdle, Olga
AU  - Guzsvány, Valéria
AU  - Škorić, Dušan
AU  - Anojčić, Jasmina
AU  - Jovanov, Pavle
AU  - Avramov Ivić, Milka
AU  - Csanadi, Janos
AU  - Kónya, Zoltán
AU  - Petrović, Slobodan D.
AU  - Bobrowski, Andrzej
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1964
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  - Oxford : Pergamon-Elsevier Science Ltd
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
VL  - 191
SP  - 44
EP  - 54
DO  - 10.1016/j.electacta.2015.12.207
ER  - 
@article{
author = "Vajdle, Olga and Guzsvány, Valéria and Škorić, Dušan and Anojčić, Jasmina and Jovanov, Pavle and Avramov Ivić, Milka and Csanadi, Janos and Kónya, Zoltán and Petrović, Slobodan D. 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 = "Oxford : Pergamon-Elsevier Science Ltd",
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",
volume = "191",
pages = "44-54",
doi = "10.1016/j.electacta.2015.12.207"
}
Vajdle, O., Guzsvány, V., Škorić, D., Anojčić, J., Jovanov, P., Avramov Ivić, M., Csanadi, J., Kónya, Z., Petrović, S. D.,& 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
Oxford : Pergamon-Elsevier Science Ltd., 191, 44-54.
https://doi.org/10.1016/j.electacta.2015.12.207
Vajdle O, Guzsvány V, Škorić D, Anojčić J, Jovanov P, Avramov Ivić M, Csanadi J, Kónya Z, Petrović SD, 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, Škorić, Dušan, Anojčić, Jasmina, Jovanov, Pavle, Avramov Ivić, Milka, Csanadi, Janos, Kónya, Zoltán, Petrović, Slobodan D., 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

Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis

Bjelaković, Mira; Krstić, Natalija; Tinant, Bernard; Kalvoda, Jaroslav; Csanadi, Janos; Pavlović, Vladimir D.

(Wiley, 2005)

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Tinant, Bernard
AU  - Kalvoda, Jaroslav
AU  - Csanadi, Janos
AU  - Pavlović, Vladimir D.
PY  - 2005
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4186
AB  - The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution.
PB  - Wiley
T2  - Helvetica Chimica Acta
T1  - Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis
VL  - 88
IS  - 10
SP  - 2812
EP  - 2821
DO  - 10.1002/hlca.200590221
ER  - 
@article{
author = "Bjelaković, Mira and Krstić, Natalija and Tinant, Bernard and Kalvoda, Jaroslav and Csanadi, Janos and Pavlović, Vladimir D.",
year = "2005",
abstract = "The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution.",
publisher = "Wiley",
journal = "Helvetica Chimica Acta",
title = "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis",
volume = "88",
number = "10",
pages = "2812-2821",
doi = "10.1002/hlca.200590221"
}
Bjelaković, M., Krstić, N., Tinant, B., Kalvoda, J., Csanadi, J.,& Pavlović, Vladimir D.. (2005). Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta
Wiley., 88(10), 2812-2821.
https://doi.org/10.1002/hlca.200590221
Bjelaković M, Krstić N, Tinant B, Kalvoda J, Csanadi J, Pavlović V. Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta. 2005;88(10):2812-2821.
doi:10.1002/hlca.200590221 .
Bjelaković, Mira, Krstić, Natalija, Tinant, Bernard, Kalvoda, Jaroslav, Csanadi, Janos, Pavlović, Vladimir D., "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis" in Helvetica Chimica Acta, 88, no. 10 (2005):2812-2821,
https://doi.org/10.1002/hlca.200590221 . .
3
3
3