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Molecules
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Selectivity and Theoretical Studies of Cycloaddition Reactions
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Selectivity and Theoretical Studies of Cycloaddition Reactions

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Computational and Theoretical Chemistry".

Deadline for manuscript submissions: 31 January 2027 | Viewed by 3022

Editors

Prof. Dr. Radomir Jasiński

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Guest Editor
Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, Poland
Interests: cycloaddition reactions; nitrocompounds; cycloaddition; heterocycles; reaction mechanisms; organic reactivity; DFT calculations
Special Issues, Collections and Topics in MDPI journals
Dr. Agnieszka Łapczuk

E-Mail Website
Guest Editor
Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, Poland
Interests: cycloaddition reactions; heterocycles; nitrocompounds; reaction mechanisms; regio- and stereoselectivity; DFT calculations; molecular electron density theory (MEDT)
Special Issues, Collections and Topics in MDPI journals
Dr. Ewa Dresler

E-Mail Website
Guest Editor
Łukasiewicz Research Network—Institute for Renewable Resources Chemistry, Energetyków 9, 47-225 Kędzierzyn-Koźle, Poland
Interests: synthesis; organic chemistry; environmental science; catalysis; cycloaddition reactions
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Cycloaddition reactions represent a cornerstone in synthetic organic chemistry, enabling the efficient construction of cyclic frameworks with full atomic economy. This Special Issue focuses on the selectivity (chemo-, regio-, and stereoselectivity) and theoretical studies of cycloaddition reactions, highlighting recent advances in mechanistic insights, computational modeling, and predictive design. Contributions will explore the interplay between electronic, steric, and catalytic control in governing reaction pathways, as well as the application of modern quantum chemical methods (e.g., DFT, MD, and machine learning) to elucidate pseudocyclic processes. Topics include [2+1], [2+2], [3+2], [4+2], [4+3], and higher-order cycloadditions, asymmetric variants, and emerging catalytic systems. By integrating experimental and theoretical perspectives, this Special Issue provides a comprehensive resource for researchers pursuing precision in carbo- and heterocyclic molecule synthesis.

Prof. Dr. Radomir Jasiński
Dr. Agnieszka Łapczuk
Dr. Ewa Dresler
Guest Editors

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • cycloaddition
  • selectivity
  • density functional theory (DFT)
  • reaction mechanisms
  • catalysis
  • stereocontrol

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Published Papers (2 papers)

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Research

22 pages, 1704 KB  
Article
Mechanistic Insights into Lewis Acid-Catalyzed Formal [3 + 2] Cycloadditions of Aziridines: A Molecular Electron Density Theory Study
by Luis R. Domingo, Patricia Pérez and Maria José Aurell
Molecules 2026, 31(3), 509; https://doi.org/10.3390/molecules31030509 - 2 Feb 2026
Cited by 1 | Viewed by 1053
Abstract
The Lewis acid (LA)-promoted formal [3 + 2] cycloaddition (32CA) reaction of 2-phenyl-1-tosylaziridine (2PTA) with ketone has been studied within the framework of Molecular Electron Density Theory (MEDT) at the ωB97X-D/6-311G(d,p) computational level in dichloromethane. This formal 32CA reaction proceeds through a [...] Read more.
The Lewis acid (LA)-promoted formal [3 + 2] cycloaddition (32CA) reaction of 2-phenyl-1-tosylaziridine (2PTA) with ketone has been studied within the framework of Molecular Electron Density Theory (MEDT) at the ωB97X-D/6-311G(d,p) computational level in dichloromethane. This formal 32CA reaction proceeds through a stepwise mechanism, involving an initial BF3 LA-promoted aziridine ring-opening process, followed by a ring-closure process to yield the 1,3-oxazolidine product. The activation enthalpy of the most favorable C2–N1 breaking bond step, ΔH≠ = 6.42 kcal·mol−1, is 20.98 kcal·mol−1 lower than that of the non-catalyzed process, the aziridine ring-opening process being totally C2 regioselective and stereospecific. A topological analysis of the electron localization function (ELF) reveals that the most favorable transition state structure exhibits C2 carbocationic character; in this structure, the C2–N1 single bond has broken, while the C2–O4 single bond has not yet formed. A relative interacting atomic energy (RIAE) analysis of the aziridine ring-opening step reveals that the stabilization of the sulfonamide/LA leaving group and that of the ketone frameworks are the key factors responsible for the reduction in the activation barrier in the presence of LAs. LAs shift the mechanism of the aziridine ring-opening process from SN2-like in the non-catalyzed reaction to SN1-like in the LA-promoted process, which occurs with the inversion of the C2 carbon. Full article
(This article belongs to the Special Issue Selectivity and Theoretical Studies of Cycloaddition Reactions)
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20 pages, 2363 KB  
Article
On the Question of the Application Potential and the Molecular Mechanism of the Formation of 1,3-Diaryl-5-Nitropyrazoles from Trichloromethylated Diarylnitropyrazolines
by Karolina Kula and Radomir Jasiński
Molecules 2025, 30(21), 4306; https://doi.org/10.3390/molecules30214306 - 5 Nov 2025
Cited by 3 | Viewed by 1331
Abstract
The molecular mechanism of the formation of 1,3-diaryl-5-nitropyrazoles via a CHCl3-elimination reaction was investigated using ωB97xD/6-31+G(d,p) (PCM) calculations. It was found that, regardless of the polarity of the reaction environment or the nature of the substituents on the phenyl rings of [...] Read more.
The molecular mechanism of the formation of 1,3-diaryl-5-nitropyrazoles via a CHCl3-elimination reaction was investigated using ωB97xD/6-31+G(d,p) (PCM) calculations. It was found that, regardless of the polarity of the reaction environment or the nature of the substituents on the phenyl rings of the starting molecules, the elimination process proceeds through a single-step mechanism characterized by an extremely asynchronous transition state. The ELF (Electron Localization Function) analysis of selected critical structures confirms the proposed mechanism and reveals a pronounced reorganization of electrons within the heterocyclic ring. The in silico analysis based on ADME (Activity, Distribution, Metabolism, and Excretion) and PASS (Prediction of Activity Spectra for Substances) predictions indicates that the title 1,3-diaryl-5-nitropyrazoles exhibit promising biological potential, showing inhibitory activity against both oxidoreductases and proteases. The most consistent targets include hyponitrite reductase, (R)-6-hydroxynicotine oxidase, acrocylindropepsin, saccharopepsin, and chymosin. Thus, the presented CHCl3-elimination provides an efficient and versatile route to functionalized pyrazoles, and, together with their promising bioactivity, confirms the utility of this approach for their synthesis. Full article
(This article belongs to the Special Issue Selectivity and Theoretical Studies of Cycloaddition Reactions)
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