Dr. Karolina Kula
Department of Organic Chemistry and Technology (Cracow University of Technology)
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Academic Career Length
12Years (2015-Present)
(Calculated once Scilit publication data is synced: current year − year of first publication + 1)
Representative Publications
View All Publications2 September 2020 in European Journal of Organic Chemistry
Journal Article
Journal Article
Karolina Kula
Agnieszka ŁapczukMSMikołaj Jacek Sadowski
Mikołaj Jacek SadowskiJKJowita Kras
Jowita KrasKZKarolina Zawadzińska
Karolina Zawadzińska
Radomir Jasinski +3
Experimental and theoretical studies on the reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromophenyl)-C-arylnitrylimine were performed. It was found that the title process unexpectedly led to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of the expected Δ2-pyrazoline molecular system. This was the result of a unique CHCl3 elimination process. The observed mechanism of transformation was explained in the framework of the molecular electron density theory (MEDT). The theoretical results showed that both of the possible channels of [3 + 2] cycloaddition were favorable from a kinetic point of view, due to which the creation of 1-(4-bromophenyl)-3-aryl-4-tricholomethyl-5-nitro-Δ2-pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.
Journal Article
KZKarolina Zawadzińska
Karolina Zawadzińska
Mar Ríos-GutiérrezKarolina KulaPWPrzemysław Woliński
Przemysław Woliński
Barbara MiroslawRadomir Jasinski +1
The regioselective zw-type [3 + 2] cycloaddition (32CA) reactions of a series of aryl-substituted nitrile N-oxides (NOs) with trichloronitropropene (TNP) have been both experimentally and theoretically studied within the Molecular Electron Density Theory (MEDT). Zwitterionic NOs behave as moderate nucleophiles while TNP acts as a very strong electrophile in these polar 32CA reactions of forward electron density flux, which present moderate activation Gibbs free energies of 22.8–25.6 kcal·mol−1 and an exergonic character of 28.4 kcal·mol−1 that makes them irreversible and kinetically controlled. The most favorable reaction is that involving the most nucleophilic MeO-substituted NO. Despite Parr functions correctly predicting the experimental regioselectivity with the most favorable O-CCCl3 interaction, these reactions follow a two-stage one-step mechanism in which formation of the O-C(CCl3) bond takes place once the C-C(NO2) bond is already formed. The present MEDT concludes that the reactivity differences in the series of NOs come from their different nucleophilic activation and polar character of the reactions, rather than any mechanistic feature.
Journal Article
MSMikołaj Jacek Sadowski
Mikołaj Jacek SadowskiKarolina KulaIn recent times, interest in the chemistry of conjugated nitrodienes is still significantly increasing. In particular, the application of these compounds as building blocks to obtain heterocycles is a popular object of research. Therefore, in continuation of our research devoted to the topic of conjugated nitrodienes, experimental and quantum-chemical studies of a cycloaddition reaction between (1E,3E)-1,4-dinitro-1,3-butadiene and N-methyl azomethine ylide have been investigated. The computational results present that the tested reaction is realized through a pdr-type polar mechanism. In turn, the experimental study shows that in a course of this cycloaddition, only one reaction product in the form of 1-methyl-3-(trans-2-nitrovinyl)-Δ3-pyrroline is created. The constitution of this compound has been confirmed via spectroscopic methods. Finally, ADME analysis indicated that the synthesized Δ3-pyrroline exhibits biological potential, and it is a good drug candidate according to Lipinski, Veber and Egan rules. Nevertheless, PASS simulation showed that the compound exhibits weak antimicrobial, inhibitory and antagonist properties. Preliminary in silico research shows that although the obtained Δ3-pyrroline is not a good candidate for a drug, the presence of a nitrovinyl moiety in its structure indicates that the compound is an initial basis for further modifications.
Journal Article
MSMikołaj Jacek Sadowski
Mikołaj Jacek SadowskiBSBeata Synkiewicz-Musialska
Beata Synkiewicz-MusialskaKarolina KulaThe chemistry of conjugated nitrodienes is becoming increasingly popular. These molecules are successfully applied in cycloaddition to synthesize six-membered rings in Diels-Alder reactions. Nitrodienes can be also applied to obtain bis-compounds in [3+2] cycloaddition. Moreover, the presence of a nitro group in the structure provides a possibility of further modification of the products. The simplest symmetrical representative of conjugated nitrodienes is (1E,3E)-1,4-dinitro-1,3-butadiene. Although the first mentions of the compound date back to the early 1950s, the compound has not yet been examined thoroughly enough. Therefore, in this article, a comprehensive study of (1E,3E)-1,4-dinitro-1,3-butadiene has been described. For this purpose, an experimental study including the synthesis process as well as an evaluation of the spectral characteristics has been conducted. So as to better understand the properties of this compound, a computational study of reactivity indices based on MEDT and also an assessment of pharmacokinetics and biological activity according to ADME and PASS methodologies have been made. On this basis, some future application trends of (1E,3E)-1,4-dinitro-1,3-butadiene have been proposed.
1 March 2020 in Journal of Molecular Structure
Journal Article
Karolina KulaJDJoanna Dobosz
Joanna Dobosz
Radomir Jasinski
Agnieszka Kącka-ZychAŁAgnieszka Łapczuk-Krygier
Agnieszka Łapczuk-Krygier
Oleg M. Demchuk +1
About Me
PhD Eng. Karolina Kula is an Assistant Professor at the Faculty of Chemical Engineering and Technology at CUT (Cracow, Poland). Her scientific interests focus on the regio- and stereochemistry, kinetics, and mechanisms of cycloaddition reactions, particularly those involving nitroalkenes and nitrodienes. Her research combines experimental investigations with theoretical studies based on quantum-chemical calculations within the framework of Molecular Electron Density Theory. Alongside this, she is involved in the synthesis of molecules with biological potential and the utilization of GHGs in organic synthesis. She has authored nearly 50 publications (cumulative IF = 126.7) and has actively participated in nearly 60 national and international conferences. In addition, she actively participates in the scientific evaluation of manuscripts (Editorial Board (3) of Chem. Heterocycl. Compd., Curr. Org. Chem., Curr. Chem. Lett.; Reviewer Board (3) of IJMS, Organics, Materials; Early Career Editorial Board (2) of Molecules, Prog. React. Kinet. Mech.; Guest Editor (5) in IJMS, Discov. Appl. Sci., Chem. Heterocycl. Compd., Molecules (twice), over 450 peer reviews documented in WoS). Besides,she is actively engaged in academic education. She is the author of 3 academic monographs. She has also supervised 5 BEng theses, 3 MSc theses and co-supervises 2 PhD theses. Her teaching excellence has been recognized through numerous awards and distinctions.