Džambaski, Zdravko

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  • Džambaski, Zdravko (9)
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Author's Bibliography

Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes

Džambaski, Zdravko; Baranac-Stojanović, Marija

(Wiley-V C H Verlag Gmbh, Weinheim, 2017)

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Baranac-Stojanović, Marija
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2425
AB  - We have studied pi electron delocalization in electron- deficient alkenes and push- pull alkenes by means of natural bond orbital analysis at the B3LYP/6-311+ G(d,p) level. The study revealed that the rarely mentioned pi electron donation from an electron-accepting group (Acc) toward the C=C double bond in push-pull alkenes and electron-deficient alkenes can provide up to 10% of total pi electron stabilizing energy of a push-pull system and as much as 45% in a strongly electron-deficient tetracyanoethene. The Acc - gt  C= C bond pi electron donation is more intense in s-trans than in s-cis conformational arrangement, but is less dependent on Z/E isomerism in push-pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COO-groups contribute the largest percent of stabilizing energy and NO2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc - gt  C= C bond p electron delocalization to a system stabilization. A difference in pi*(C=C) orbital occupancy between isomers can be related with their chemical reactivity.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - CHEMISTRYSELECT
T1  - Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes
VL  - 2
IS  - 1
SP  - 42
EP  - 50
DO  - 10.1002/slct.201601661
UR  - Kon_3241
ER  - 
@article{
author = "Džambaski, Zdravko and Baranac-Stojanović, Marija",
year = "2017",
abstract = "We have studied pi electron delocalization in electron- deficient alkenes and push- pull alkenes by means of natural bond orbital analysis at the B3LYP/6-311+ G(d,p) level. The study revealed that the rarely mentioned pi electron donation from an electron-accepting group (Acc) toward the C=C double bond in push-pull alkenes and electron-deficient alkenes can provide up to 10% of total pi electron stabilizing energy of a push-pull system and as much as 45% in a strongly electron-deficient tetracyanoethene. The Acc - gt  C= C bond pi electron donation is more intense in s-trans than in s-cis conformational arrangement, but is less dependent on Z/E isomerism in push-pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COO-groups contribute the largest percent of stabilizing energy and NO2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc - gt  C= C bond p electron delocalization to a system stabilization. A difference in pi*(C=C) orbital occupancy between isomers can be related with their chemical reactivity.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "CHEMISTRYSELECT",
title = "Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes",
volume = "2",
number = "1",
pages = "42-50",
doi = "10.1002/slct.201601661",
url = "Kon_3241"
}
Džambaski, Z.,& Baranac-Stojanović, M.. (2017). Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. in CHEMISTRYSELECT
Wiley-V C H Verlag Gmbh, Weinheim., 2(1), 42-50.
https://doi.org/10.1002/slct.201601661
Kon_3241
Džambaski Z, Baranac-Stojanović M. Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes. in CHEMISTRYSELECT. 2017;2(1):42-50.
doi:10.1002/slct.201601661
Kon_3241 .
Džambaski, Zdravko, Baranac-Stojanović, Marija, "Electron Delocalization in Electron-Deficient Alkenes and Push-Pull Alkenes" in CHEMISTRYSELECT, 2, no. 1 (2017):42-50,
https://doi.org/10.1002/slct.201601661 .,
Kon_3241 .
1
4
3
4

4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity

Stojanović, Milovan; Džambaski, Zdravko; Bondžić, Bojan; Aleksić, Jovana; Baranac-Stojanović, Marija

(Bentham Science Publ Ltd, Sharjah, 2014)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2014
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1810
AB  - 4-Oxothiazolidine core, owing to the wide range of pharmacological activities exhibited by its derivatives, has been recognized as an important structural motif in biologically active compounds. A subclass constitutes 4-oxothiazolidines with an exocyclic C=C double bond at the C(2)-position. Some of these derivatives are registered as active substances for the treatment of various diseases, such as Ralitoline, an antiepileptic, Etozolin, a diuretic, and Piprozolin, a choleretic. The exocyclic C=C double bond in these compounds contains one or two electron-accepting groups at its other end, so that they also belong to the class of the so-called push-pull alkenes. In the case of the nitrogen-unsubstituted molecules, the enamino tautomeric form with the exocyclic double bond is stabilized by the extended electron delocalization arising from the push-pull effect. In the absence of push-pull effect, the imino form would dominate. Therefore, these compounds exhibit properties characteristic for both 4-oxothiazolidine ring and push-pull alkenes. They are also proved to be useful synthetic interamediates for the formation of various mono- and polyheterocycles. The importance of 4-oxothiazolidine derivatives is witnessed by several review articles, the latest published in 2012, mainly dealing with the chemistry and biological activity of various 2-imino, 2-oxo, 2-thioxo and 2-alkyl(aryl)-substituted compounds. The lack of a comprehensive review on 2-alkylidene-4-oxothiazolidines has prompted us to collect the literature covering their synthesis, structure, reactivity and biological activity. Derivatives with two exocyclic C=C double bonds are included, too.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Current Organic Chemistry
T1  - 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity
VL  - 18
IS  - 9
SP  - 1108
EP  - 1148
DO  - 10.2174/138527281809140624120436
UR  - Kon_2693
ER  - 
@article{
author = "Stojanović, Milovan and Džambaski, Zdravko and Bondžić, Bojan and Aleksić, Jovana and Baranac-Stojanović, Marija",
year = "2014",
abstract = "4-Oxothiazolidine core, owing to the wide range of pharmacological activities exhibited by its derivatives, has been recognized as an important structural motif in biologically active compounds. A subclass constitutes 4-oxothiazolidines with an exocyclic C=C double bond at the C(2)-position. Some of these derivatives are registered as active substances for the treatment of various diseases, such as Ralitoline, an antiepileptic, Etozolin, a diuretic, and Piprozolin, a choleretic. The exocyclic C=C double bond in these compounds contains one or two electron-accepting groups at its other end, so that they also belong to the class of the so-called push-pull alkenes. In the case of the nitrogen-unsubstituted molecules, the enamino tautomeric form with the exocyclic double bond is stabilized by the extended electron delocalization arising from the push-pull effect. In the absence of push-pull effect, the imino form would dominate. Therefore, these compounds exhibit properties characteristic for both 4-oxothiazolidine ring and push-pull alkenes. They are also proved to be useful synthetic interamediates for the formation of various mono- and polyheterocycles. The importance of 4-oxothiazolidine derivatives is witnessed by several review articles, the latest published in 2012, mainly dealing with the chemistry and biological activity of various 2-imino, 2-oxo, 2-thioxo and 2-alkyl(aryl)-substituted compounds. The lack of a comprehensive review on 2-alkylidene-4-oxothiazolidines has prompted us to collect the literature covering their synthesis, structure, reactivity and biological activity. Derivatives with two exocyclic C=C double bonds are included, too.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Current Organic Chemistry",
title = "4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity",
volume = "18",
number = "9",
pages = "1108-1148",
doi = "10.2174/138527281809140624120436",
url = "Kon_2693"
}
Stojanović, M., Džambaski, Z., Bondžić, B., Aleksić, J.,& Baranac-Stojanović, M.. (2014). 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity. in Current Organic Chemistry
Bentham Science Publ Ltd, Sharjah., 18(9), 1108-1148.
https://doi.org/10.2174/138527281809140624120436
Kon_2693
Stojanović M, Džambaski Z, Bondžić B, Aleksić J, Baranac-Stojanović M. 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity. in Current Organic Chemistry. 2014;18(9):1108-1148.
doi:10.2174/138527281809140624120436
Kon_2693 .
Stojanović, Milovan, Džambaski, Zdravko, Bondžić, Bojan, Aleksić, Jovana, Baranac-Stojanović, Marija, "4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity" in Current Organic Chemistry, 18, no. 9 (2014):1108-1148,
https://doi.org/10.2174/138527281809140624120436 .,
Kon_2693 .
11
9
10

Supplementary data for article: Džambaski, Z.; Toljic, D.; Bondzic, B.; Marković, R.; Baranac-Stojanović, M. Unusual Mode of Reactivity of 2-Alkylidene-4-Oxothiazolidine S-Oxides under the Pummerer Reaction Conditions. Tetrahedron 2013, 69 (46), 9819–9825. https://doi.org/10.1016/j.tet.2013.09.004

Džambaski, Zdravko; Toljić, Đorđe; Bondžić, Bojan; Marković, Rade; Baranac-Stojanović, Marija

(Pergamon-Elsevier Science Ltd, Oxford, 2013)

TY  - DATA
AU  - Džambaski, Zdravko
AU  - Toljić, Đorđe
AU  - Bondžić, Bojan
AU  - Marković, Rade
AU  - Baranac-Stojanović, Marija
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3558
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Supplementary data for article: Džambaski, Z.; Toljic, D.; Bondzic, B.; Marković, R.; Baranac-Stojanović, M. Unusual Mode of Reactivity of 2-Alkylidene-4-Oxothiazolidine S-Oxides under the Pummerer Reaction Conditions. Tetrahedron 2013, 69 (46), 9819–9825. https://doi.org/10.1016/j.tet.2013.09.004
ER  - 
@misc{
author = "Džambaski, Zdravko and Toljić, Đorđe and Bondžić, Bojan and Marković, Rade and Baranac-Stojanović, Marija",
year = "2013",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Supplementary data for article: Džambaski, Z.; Toljic, D.; Bondzic, B.; Marković, R.; Baranac-Stojanović, M. Unusual Mode of Reactivity of 2-Alkylidene-4-Oxothiazolidine S-Oxides under the Pummerer Reaction Conditions. Tetrahedron 2013, 69 (46), 9819–9825. https://doi.org/10.1016/j.tet.2013.09.004"
}
Džambaski, Z., Toljić, Đ., Bondžić, B., Marković, R.,& Baranac-Stojanović, M.. (2013). Supplementary data for article: Džambaski, Z.; Toljic, D.; Bondzic, B.; Marković, R.; Baranac-Stojanović, M. Unusual Mode of Reactivity of 2-Alkylidene-4-Oxothiazolidine S-Oxides under the Pummerer Reaction Conditions. Tetrahedron 2013, 69 (46), 9819–9825. https://doi.org/10.1016/j.tet.2013.09.004. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford..
Džambaski Z, Toljić Đ, Bondžić B, Marković R, Baranac-Stojanović M. Supplementary data for article: Džambaski, Z.; Toljic, D.; Bondzic, B.; Marković, R.; Baranac-Stojanović, M. Unusual Mode of Reactivity of 2-Alkylidene-4-Oxothiazolidine S-Oxides under the Pummerer Reaction Conditions. Tetrahedron 2013, 69 (46), 9819–9825. https://doi.org/10.1016/j.tet.2013.09.004. in Tetrahedron. 2013;..
Džambaski, Zdravko, Toljić, Đorđe, Bondžić, Bojan, Marković, Rade, Baranac-Stojanović, Marija, "Supplementary data for article: Džambaski, Z.; Toljic, D.; Bondzic, B.; Marković, R.; Baranac-Stojanović, M. Unusual Mode of Reactivity of 2-Alkylidene-4-Oxothiazolidine S-Oxides under the Pummerer Reaction Conditions. Tetrahedron 2013, 69 (46), 9819–9825. https://doi.org/10.1016/j.tet.2013.09.004" in Tetrahedron (2013).

Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions

Džambaski, Zdravko; Toljić, Đorđe; Bondžić, Bojan; Marković, Rade; Baranac-Stojanović, Marija

(Pergamon-Elsevier Science Ltd, Oxford, 2013)

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Toljić, Đorđe
AU  - Bondžić, Bojan
AU  - Marković, Rade
AU  - Baranac-Stojanović, Marija
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1434
AB  - The reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions, using Ac2O, TFAA, SOCl2 and SOBr2 as initiators, has been examined. Almost all reactions proceeded with absolute regioselectivity yielding alpha-substituted sulfides or vinyl-chloro derivatives. The mechanism for the formation of the latter products was postulated and proved experimentally.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions
VL  - 69
IS  - 46
SP  - 9819
EP  - 9825
DO  - 10.1016/j.tet.2013.09.004
UR  - Kon_2554
ER  - 
@article{
author = "Džambaski, Zdravko and Toljić, Đorđe and Bondžić, Bojan and Marković, Rade and Baranac-Stojanović, Marija",
year = "2013",
abstract = "The reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions, using Ac2O, TFAA, SOCl2 and SOBr2 as initiators, has been examined. Almost all reactions proceeded with absolute regioselectivity yielding alpha-substituted sulfides or vinyl-chloro derivatives. The mechanism for the formation of the latter products was postulated and proved experimentally.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions",
volume = "69",
number = "46",
pages = "9819-9825",
doi = "10.1016/j.tet.2013.09.004",
url = "Kon_2554"
}
Džambaski, Z., Toljić, Đ., Bondžić, B., Marković, R.,& Baranac-Stojanović, M.. (2013). Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 69(46), 9819-9825.
https://doi.org/10.1016/j.tet.2013.09.004
Kon_2554
Džambaski Z, Toljić Đ, Bondžić B, Marković R, Baranac-Stojanović M. Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions. in Tetrahedron. 2013;69(46):9819-9825.
doi:10.1016/j.tet.2013.09.004
Kon_2554 .
Džambaski, Zdravko, Toljić, Đorđe, Bondžić, Bojan, Marković, Rade, Baranac-Stojanović, Marija, "Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions" in Tetrahedron, 69, no. 46 (2013):9819-9825,
https://doi.org/10.1016/j.tet.2013.09.004 .,
Kon_2554 .
4
4
4

2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry

Džambaski, Zdravko; Marković, Rade; Kleinpeter, Erich; Baranac-Stojanović, Marija

(Pergamon-Elsevier Science Ltd, Oxford, 2013)

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Marković, Rade
AU  - Kleinpeter, Erich
AU  - Baranac-Stojanović, Marija
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1371
AB  - A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)- gt sigma*(S-O) interaction versus the weaker sigma(C-C)- gt sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry
VL  - 69
IS  - 31
SP  - 6436
EP  - 6447
DO  - 10.1016/j.tet.2013.05.087
UR  - Kon_2491
ER  - 
@article{
author = "Džambaski, Zdravko and Marković, Rade and Kleinpeter, Erich and Baranac-Stojanović, Marija",
year = "2013",
abstract = "A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)- gt sigma*(S-O) interaction versus the weaker sigma(C-C)- gt sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry",
volume = "69",
number = "31",
pages = "6436-6447",
doi = "10.1016/j.tet.2013.05.087",
url = "Kon_2491"
}
Džambaski, Z., Marković, R., Kleinpeter, E.,& Baranac-Stojanović, M.. (2013). 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 69(31), 6436-6447.
https://doi.org/10.1016/j.tet.2013.05.087
Kon_2491
Džambaski Z, Marković R, Kleinpeter E, Baranac-Stojanović M. 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry. in Tetrahedron. 2013;69(31):6436-6447.
doi:10.1016/j.tet.2013.05.087
Kon_2491 .
Džambaski, Zdravko, Marković, Rade, Kleinpeter, Erich, Baranac-Stojanović, Marija, "2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry" in Tetrahedron, 69, no. 31 (2013):6436-6447,
https://doi.org/10.1016/j.tet.2013.05.087 .,
Kon_2491 .
7
9
10

Supplementary data for article: Džambaski, Z.; Markovic, R.; Kleinpeter, E.; Baranac-Stojanović, M. 2-Alkylidene-4-Oxothiazolidine S-Oxides: Synthesis and Stereochemistry. Tetrahedron 2013, 69 (31), 6436–6447. https://doi.org/10.1016/j.tet.2013.05.087

Džambaski, Zdravko; Marković, Rade; Kleinpeter, Erich; Baranac-Stojanović, Marija

(Pergamon-Elsevier Science Ltd, Oxford, 2013)

TY  - DATA
AU  - Džambaski, Zdravko
AU  - Marković, Rade
AU  - Kleinpeter, Erich
AU  - Baranac-Stojanović, Marija
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3464
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Supplementary data for article: Džambaski, Z.; Markovic, R.; Kleinpeter, E.; Baranac-Stojanović, M. 2-Alkylidene-4-Oxothiazolidine S-Oxides: Synthesis and Stereochemistry. Tetrahedron 2013, 69 (31), 6436–6447. https://doi.org/10.1016/j.tet.2013.05.087
ER  - 
@misc{
author = "Džambaski, Zdravko and Marković, Rade and Kleinpeter, Erich and Baranac-Stojanović, Marija",
year = "2013",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Supplementary data for article: Džambaski, Z.; Markovic, R.; Kleinpeter, E.; Baranac-Stojanović, M. 2-Alkylidene-4-Oxothiazolidine S-Oxides: Synthesis and Stereochemistry. Tetrahedron 2013, 69 (31), 6436–6447. https://doi.org/10.1016/j.tet.2013.05.087"
}
Džambaski, Z., Marković, R., Kleinpeter, E.,& Baranac-Stojanović, M.. (2013). Supplementary data for article: Džambaski, Z.; Markovic, R.; Kleinpeter, E.; Baranac-Stojanović, M. 2-Alkylidene-4-Oxothiazolidine S-Oxides: Synthesis and Stereochemistry. Tetrahedron 2013, 69 (31), 6436–6447. https://doi.org/10.1016/j.tet.2013.05.087. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford..
Džambaski Z, Marković R, Kleinpeter E, Baranac-Stojanović M. Supplementary data for article: Džambaski, Z.; Markovic, R.; Kleinpeter, E.; Baranac-Stojanović, M. 2-Alkylidene-4-Oxothiazolidine S-Oxides: Synthesis and Stereochemistry. Tetrahedron 2013, 69 (31), 6436–6447. https://doi.org/10.1016/j.tet.2013.05.087. in Tetrahedron. 2013;..
Džambaski, Zdravko, Marković, Rade, Kleinpeter, Erich, Baranac-Stojanović, Marija, "Supplementary data for article: Džambaski, Z.; Markovic, R.; Kleinpeter, E.; Baranac-Stojanović, M. 2-Alkylidene-4-Oxothiazolidine S-Oxides: Synthesis and Stereochemistry. Tetrahedron 2013, 69 (31), 6436–6447. https://doi.org/10.1016/j.tet.2013.05.087" in Tetrahedron (2013).

Estimation of Lipophilicity of N-Substituted 2-Alkylidene-4-Oxothiazolidines by Means of Reversed-Phase Thin-Layer Chromatography

Dabić-Zagorac, Dragana; Natić, Maja; Džambaski, Zdravko; Stojanović, Milovan; Marković, Rade; Milojković-Opsenica, Dušanka; Tešić, Živoslav Lj.

(Taylor & Francis Inc, Philadelphia, 2011)

TY  - JOUR
AU  - Dabić-Zagorac, Dragana
AU  - Natić, Maja
AU  - Džambaski, Zdravko
AU  - Stojanović, Milovan
AU  - Marković, Rade
AU  - Milojković-Opsenica, Dušanka
AU  - Tešić, Živoslav Lj.
PY  - 2011
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1346
AB  - The chromatographic behavior of 23 new 2-alkylidene-4-oxothiazolidine derivatives was investigated by means of the reversed-phase thin-layer chromatography (RP TLC) on the C18 and CN stationary phases. Binary mixtures of methanol-water, acetonitrile-water, and tetrahydrofuran-water were used as mobile phases. Linear relationships between the volume fraction of the organic mobile phase modifier and the RM values were established for each solute with high correlation coefficient values (r0.99). The investigated 4-oxothiazolidines are a congeneric set of compounds, and significant correlations were obtained between the chromatographically determined [image omitted] and m values. The lipophilicity parameters obtained from the reversed-phase experiments were compared with the calculated log P values. Some of these correlations offer very good predicting models, which are important for a better understanding of the relationships between chemical structure and retention, and can prove helpful in the structure-activity studies as well. Finally, our investigation was focused on chemometric processing of the retention data in different chromatographic systems. To this effect, Principal Component Analysis (PCA) was performed, yielding the results helpful in interpretation of interactions among investigated substances, binary mobile phases, and the two different stationary phases.
PB  - Taylor & Francis Inc, Philadelphia
T2  - Journal of Liquid Chromatography and Related Technologies
T1  - Estimation of Lipophilicity of N-Substituted 2-Alkylidene-4-Oxothiazolidines by Means of Reversed-Phase Thin-Layer Chromatography
VL  - 34
IS  - 10-11
SP  - 791
EP  - 804
DO  - 10.1080/10826076.2011.571157
UR  - Kon_2184
ER  - 
@article{
author = "Dabić-Zagorac, Dragana and Natić, Maja and Džambaski, Zdravko and Stojanović, Milovan and Marković, Rade and Milojković-Opsenica, Dušanka and Tešić, Živoslav Lj.",
year = "2011",
abstract = "The chromatographic behavior of 23 new 2-alkylidene-4-oxothiazolidine derivatives was investigated by means of the reversed-phase thin-layer chromatography (RP TLC) on the C18 and CN stationary phases. Binary mixtures of methanol-water, acetonitrile-water, and tetrahydrofuran-water were used as mobile phases. Linear relationships between the volume fraction of the organic mobile phase modifier and the RM values were established for each solute with high correlation coefficient values (r0.99). The investigated 4-oxothiazolidines are a congeneric set of compounds, and significant correlations were obtained between the chromatographically determined [image omitted] and m values. The lipophilicity parameters obtained from the reversed-phase experiments were compared with the calculated log P values. Some of these correlations offer very good predicting models, which are important for a better understanding of the relationships between chemical structure and retention, and can prove helpful in the structure-activity studies as well. Finally, our investigation was focused on chemometric processing of the retention data in different chromatographic systems. To this effect, Principal Component Analysis (PCA) was performed, yielding the results helpful in interpretation of interactions among investigated substances, binary mobile phases, and the two different stationary phases.",
publisher = "Taylor & Francis Inc, Philadelphia",
journal = "Journal of Liquid Chromatography and Related Technologies",
title = "Estimation of Lipophilicity of N-Substituted 2-Alkylidene-4-Oxothiazolidines by Means of Reversed-Phase Thin-Layer Chromatography",
volume = "34",
number = "10-11",
pages = "791-804",
doi = "10.1080/10826076.2011.571157",
url = "Kon_2184"
}
Dabić-Zagorac, D., Natić, M., Džambaski, Z., Stojanović, M., Marković, R., Milojković-Opsenica, D.,& Tešić, Ž. Lj.. (2011). Estimation of Lipophilicity of N-Substituted 2-Alkylidene-4-Oxothiazolidines by Means of Reversed-Phase Thin-Layer Chromatography. in Journal of Liquid Chromatography and Related Technologies
Taylor & Francis Inc, Philadelphia., 34(10-11), 791-804.
https://doi.org/10.1080/10826076.2011.571157
Kon_2184
Dabić-Zagorac D, Natić M, Džambaski Z, Stojanović M, Marković R, Milojković-Opsenica D, Tešić ŽL. Estimation of Lipophilicity of N-Substituted 2-Alkylidene-4-Oxothiazolidines by Means of Reversed-Phase Thin-Layer Chromatography. in Journal of Liquid Chromatography and Related Technologies. 2011;34(10-11):791-804.
doi:10.1080/10826076.2011.571157
Kon_2184 .
Dabić-Zagorac, Dragana, Natić, Maja, Džambaski, Zdravko, Stojanović, Milovan, Marković, Rade, Milojković-Opsenica, Dušanka, Tešić, Živoslav Lj., "Estimation of Lipophilicity of N-Substituted 2-Alkylidene-4-Oxothiazolidines by Means of Reversed-Phase Thin-Layer Chromatography" in Journal of Liquid Chromatography and Related Technologies, 34, no. 10-11 (2011):791-804,
https://doi.org/10.1080/10826076.2011.571157 .,
Kon_2184 .
6
9
8

Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions

Džambaski, Zdravko; Stojanović, Milovan; Baranac-Stojanović, Marija; Minić, Dragica M.; Marković, Rade

(Serbian Chemical Soc, Belgrade, 2011)

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
AU  - Minić, Dragica M.
AU  - Marković, Rade
PY  - 2011
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1331
AB  - Configurational isomerization of stereo-defined 5-substituted and un-substituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by H-1-NMR spectroscopy, X-ray powder crystallography and differential scanning calorimetry (DSC). The Z/E composition can be rationalized in terms of non-covalent interactions, involving intermolecular and intramolccular hydrogen bonding and directional non-bonded 1,5-type S center dot center dot center dot O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z - gt  E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions
VL  - 76
IS  - 3
SP  - 317
EP  - 328
DO  - 10.2298/JSC100607038D
UR  - Kon_2169
ER  - 
@article{
author = "Džambaski, Zdravko and Stojanović, Milovan and Baranac-Stojanović, Marija and Minić, Dragica M. and Marković, Rade",
year = "2011",
abstract = "Configurational isomerization of stereo-defined 5-substituted and un-substituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by H-1-NMR spectroscopy, X-ray powder crystallography and differential scanning calorimetry (DSC). The Z/E composition can be rationalized in terms of non-covalent interactions, involving intermolecular and intramolccular hydrogen bonding and directional non-bonded 1,5-type S center dot center dot center dot O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z - gt  E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions",
volume = "76",
number = "3",
pages = "317-328",
doi = "10.2298/JSC100607038D",
url = "Kon_2169"
}
Džambaski, Z., Stojanović, M., Baranac-Stojanović, M., Minić, D. M.,& Marković, R.. (2011). Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 76(3), 317-328.
https://doi.org/10.2298/JSC100607038D
Kon_2169
Džambaski Z, Stojanović M, Baranac-Stojanović M, Minić DM, Marković R. Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions. in Journal of the Serbian Chemical Society. 2011;76(3):317-328.
doi:10.2298/JSC100607038D
Kon_2169 .
Džambaski, Zdravko, Stojanović, Milovan, Baranac-Stojanović, Marija, Minić, Dragica M., Marković, Rade, "Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions" in Journal of the Serbian Chemical Society, 76, no. 3 (2011):317-328,
https://doi.org/10.2298/JSC100607038D .,
Kon_2169 .
5
6
7

Quantitative structure-retention relationship of new N-substituted 2-alkylidene-4-oxothiazolidines

Dabić-Zagorac, Dragana; Natić, Maja; Džambaski, Zdravko; Marković, Rade; Milojković-Opsenica, Dušanka; Tešić, Živoslav Lj.

(Wiley-Blackwell, Malden, 2011)

TY  - JOUR
AU  - Dabić-Zagorac, Dragana
AU  - Natić, Maja
AU  - Džambaski, Zdravko
AU  - Marković, Rade
AU  - Milojković-Opsenica, Dušanka
AU  - Tešić, Živoslav Lj.
PY  - 2011
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1211
AB  - A quantitative structure-retention relationship (QSRR) was built to investigate the relationship between the structural descriptors of 23 newly synthesized N-substituted 2-alkylidene-4-oxothiazolidines and their chromatographic retention. Retention was investigated by means of the reversed-phase thin-layer chromatography (RP-TLC) on the C(18) and CN stationary phases, using methanol, acetonitrile, and tetrahydrofuran as organic modifiers. Full geometry optimization based on the Austin Model 1 (AM1) semi-empirical molecular orbital method was carried out and a set of physicochemical molecular descriptors was calculated from the optimized structures. QSRR was built by means of multiple linear regression (MLR) and partial least squares regression (PLS). The best MLR and PLS models were chosen, on the basis of comparison of the statistical parameters (squared correlation coefficient (R(2)), cross-validated coefficient (R(cv)(2)), and Fischer significance value (F) were used for MLR and the square of the multiple correlation coefficients for the calibration objects (R(2)Y (cum)) and the square of the multiple correlation coefficients for the cross-validation segments (Q(2)Y (cum)) were used for PLS models). Statistically significant and physically meaningful QSRR provided better insight on understanding the retention behavior of the new series of compounds. Lipohilicity (expressed as log P) was included in all MLR and PLS models.
PB  - Wiley-Blackwell, Malden
T2  - Journal of Separation Science
T1  - Quantitative structure-retention relationship of new N-substituted 2-alkylidene-4-oxothiazolidines
VL  - 34
IS  - 18
SP  - 2397
EP  - 2404
DO  - 10.1002/jssc.201100266
UR  - Kon_2233
ER  - 
@article{
author = "Dabić-Zagorac, Dragana and Natić, Maja and Džambaski, Zdravko and Marković, Rade and Milojković-Opsenica, Dušanka and Tešić, Živoslav Lj.",
year = "2011",
abstract = "A quantitative structure-retention relationship (QSRR) was built to investigate the relationship between the structural descriptors of 23 newly synthesized N-substituted 2-alkylidene-4-oxothiazolidines and their chromatographic retention. Retention was investigated by means of the reversed-phase thin-layer chromatography (RP-TLC) on the C(18) and CN stationary phases, using methanol, acetonitrile, and tetrahydrofuran as organic modifiers. Full geometry optimization based on the Austin Model 1 (AM1) semi-empirical molecular orbital method was carried out and a set of physicochemical molecular descriptors was calculated from the optimized structures. QSRR was built by means of multiple linear regression (MLR) and partial least squares regression (PLS). The best MLR and PLS models were chosen, on the basis of comparison of the statistical parameters (squared correlation coefficient (R(2)), cross-validated coefficient (R(cv)(2)), and Fischer significance value (F) were used for MLR and the square of the multiple correlation coefficients for the calibration objects (R(2)Y (cum)) and the square of the multiple correlation coefficients for the cross-validation segments (Q(2)Y (cum)) were used for PLS models). Statistically significant and physically meaningful QSRR provided better insight on understanding the retention behavior of the new series of compounds. Lipohilicity (expressed as log P) was included in all MLR and PLS models.",
publisher = "Wiley-Blackwell, Malden",
journal = "Journal of Separation Science",
title = "Quantitative structure-retention relationship of new N-substituted 2-alkylidene-4-oxothiazolidines",
volume = "34",
number = "18",
pages = "2397-2404",
doi = "10.1002/jssc.201100266",
url = "Kon_2233"
}
Dabić-Zagorac, D., Natić, M., Džambaski, Z., Marković, R., Milojković-Opsenica, D.,& Tešić, Ž. Lj.. (2011). Quantitative structure-retention relationship of new N-substituted 2-alkylidene-4-oxothiazolidines. in Journal of Separation Science
Wiley-Blackwell, Malden., 34(18), 2397-2404.
https://doi.org/10.1002/jssc.201100266
Kon_2233
Dabić-Zagorac D, Natić M, Džambaski Z, Marković R, Milojković-Opsenica D, Tešić ŽL. Quantitative structure-retention relationship of new N-substituted 2-alkylidene-4-oxothiazolidines. in Journal of Separation Science. 2011;34(18):2397-2404.
doi:10.1002/jssc.201100266
Kon_2233 .
Dabić-Zagorac, Dragana, Natić, Maja, Džambaski, Zdravko, Marković, Rade, Milojković-Opsenica, Dušanka, Tešić, Živoslav Lj., "Quantitative structure-retention relationship of new N-substituted 2-alkylidene-4-oxothiazolidines" in Journal of Separation Science, 34, no. 18 (2011):2397-2404,
https://doi.org/10.1002/jssc.201100266 .,
Kon_2233 .
18
20
19