How to cite this paper
Fałowska, A., Ząbkowska, M., Sambora, K., Kula, K., Łapczuk, A & Jasiński, R. (2026). Application of DFT models for the prediction of geometries and energies of the transition states in [4+2]-π -electron cycloadditions.Current Chemistry Letters, 15(1), 169-174.
References
1. Chen, S., Babazade, R., Kim, T., Han, S. & Jung, Y. (2024). A large-scale reaction dataset of mechanistic pathways of organic reactions. Sci. Data, 11(1), 863. https://doi.org/10.1038/s41597-024-03709-y
2. Domingo, L. R., Kula, K., Ríos-Gutiérrez, M. & Jasiński, R. (2021). Understanding the Participation of Fluorinated Azomethine Ylides in Carbenoid-Type [3 + 2] Cycloaddition Reactions with Ynal Systems: A Molecular Electron Density Theory Study. J. Org. Chem., 86(18), 12644–12653. https://doi.org/10.1021/acs.joc.1c01126
3. Sadowski, M. (2024). Alternative Synthetic Protocols as a Way to Mask Unreliability in Organic Chemistry Research, Case of Nitrones. Sci. Radices, 3(4), 287–293. https://doi.org/10.58332/scirad2024v3i4a05
4. Kang, P.-L. & Liu, Z.-P. (2021). Reaction prediction via atomistic simulation: from quantum mechanics to machine learning. iScience, 24(1), 102013. https://doi.org/10.1016/j.isci.2020.102013
5. Łapczuk-Krygier, A., Ponikiewski, Ł. & Jasiński, R. (2014). The crystal structure of (1RS,4RS,5RS,6SR)-5-cyano-5-nitro-6-phenyl-bicyclo[2.2.1]hept-2-ene. Crystallogr. Rep., 59(7), 961–963. https://doi.org/10.1134/S1063774514070128
6. Takahashi, J. (2023). X-Rays (Organic Synthesis). In Encyclopedia of Astrobiologyp. 3253–3254. Berlin, Heidelberg: Springer Berlin Heidelberg. https://doi.org/10.1007/978-3-662-65093-6_1696
7. Gillies, J. Z., Gillies, C. W., Lovas, F. J., Matsumura, K., Suenram, R. D., Kraka, E. & Cremer, D. (1991). Van der Waals complexes of chemically reactive gases: ozone-acetylene. J. Am. Chem. Soc., 113(17), 6408–6415. https://doi.org/10.1021/ja00017a008
8. Gillies, C. W., Gillies, J. Z., Suenram, R. D., Lovas, F. J., Kraka, E. & Cremer, D. (1991). Van der Waals complexes in 1,3-dipolar cycloaddition reactions: ozone-ethylene. J. Am. Chem. Soc., 113(7), 2412–2421. https://doi.org/10.1021/ja00007a010
9. Weisenburger, G.A., Barnhart, R.W., Clark, J.D., Dale, D.J., Hawksworth, M., Higginson, P.D., Kang, Y., Knoechel, D.J., Moon, B.S., Shaw, S.M., Taber G.P., Tickner, D. L. (2007). Determination of Reaction Heat: A Comparison of Measurement and Estimation Techniques. Org. Process Res. Dev, 11(6), 1112–1125. https://doi.org/10.1021/op700173h
10. Jasiński, R. (2015). In the searching for zwitterionic intermediates on reaction paths of [3 + 2] cycloaddition reactions between 2,2,4,4-tetramethyl-3-thiocyclobutanone S-methylide and polymerizable olefins. RSC Adv., 5(122), 101045–101048. https://doi.org/10.1039/C5RA20747A
11. Suresh, L., Lalrempuia, R., Fjermestad, T., Törnroos, K.W., Bour, J., Frache, G., Nova, A., Le Roux, E. (2025). Trapping of Key “Ate” Intermediates of NHC-Group IV Relevant to Catalyzing Copolymerization of Cyclohexene Oxide with CO 2. Organometallics, 44(1), 68–81. https://doi.org/10.1021/acs.organomet.4c00371
12. Amano, F., Nakayama, S., Suzuki, S., Yamakata, A. & Beppu, K. (2024). Trapping of Intermediates of a Photocatalytic Oxygen Evolution Reaction in Overall Water Splitting. ACS Appl. Energy Mater., 7(4), 1398–1402. https://doi.org/10.1021/acsaem.3c03172
13. Jodłowski, P.J., Chlebda, D., Piwowarczyk, E., Chrzan, M., Jędrzejczyk, R.J., Sitarz, M., Węgrzynowicz, A., Kołodziej, A., Łojewska, J. (2016). In situ and operando spectroscopic studies of sonically aided catalysts for biogas exhaust abatement. J. Mol. Struct., 1126, 132–140. https://doi.org/10.1016/j.molstruc.2016.02.039
14. Ronduda, H., Zybert, M., Patkowski, W., Ostrowski, A., Jodłowski, P., Szymański, D., Kępiński, L., Raróg-Pilecka, W. (2021). A high performance barium-promoted cobalt catalyst supported on magnesium–lanthanum mixed oxide for ammonia synthesis. RSC Adv., 11(23), 14218–14228. https://doi.org/10.1039/D1RA01584B
15. Jodłowski, P. J., Kurowski, G., Dymek, K., Oszajca, M., Piskorz, W., Hyjek, K., … Sitarz, M. (2023). From crystal phase mixture to pure metal-organic frameworks – Tuning pore and structure properties. Ultrason. Sonochem., 95, 106377. https://doi.org/10.1016/j.ultsonch.2023.106377
16. Polanyi, J. C. & Zewail, A. H. (1995). Direct Observation of the Transition State. Acc. Chem. Res., 28(3), 119–132. https://doi.org/10.1021/ar00051a005
17. Maiuri, M., Garavelli, M. & Cerullo, G. (2020). Ultrafast Spectroscopy: State of the Art and Open Challenges. J. Am. Chem. Soc., 142(1), 3–15. https://doi.org/10.1021/jacs.9b10533
18. Eyring, H. (1935). The Activated Complex in Chemical Reactions. J. Chem. Phys., 3(2), 107–115. https://doi.org/10.1063/1.1749604
19. Zawadzińska-Wrochniak, K., Kula, K., Ríos-Gutiérrez, M., Gostyński, B., Krawczyk, T. & Jasiński, R. (2025). A Comprehensive Study of the Synthesis, Spectral Characteristics, Quantum–Chemical Molecular Electron Density Theory, and In Silico Future Perspective of Novel CBr3-Functionalyzed Nitro-2-Isoxazolines Obtained via (3 + 2) Cycloaddition of (E)-3,3,3-Tribro. Molecules, 30(10), 2149. https://doi.org/10.3390/molecules30102149
20. Sadowski, M., Dresler, E. & Jasiński, R. (2025). On the Question of the Regio-Orientation, Stereo-Orientation and Molecular Mechanism in the Cascade Cycloaddition/Rearrangement/Elimination Processes Leading to Nitro-Substituted Thiopyran Analogs: DFT Computational Study. Int. J. Mol. Sci., 26(18), 8948. https://doi.org/10.3390/ijms26188948
21. Kącka‐Zych, A., Zeroual, A., Syed, A. & Bahkali, A. H. (2025). Docking Survey, ADME , Toxicological Insights, and Mechanistic Exploration of the Diels–Alder Reaction Between Hexachlorocyclopentadiene and Dichloroethylene. J. Comput. Chem., 46(10). https://doi.org/10.1002/jcc.70092
22. Woliński, P., Dresler, E. & Jasiński, R. (2025). A new mechanistic insight into the molecular mechanisms of the addition reactions of 2-aryl-3-nitro-2 H -chromenes to pyrazoles and cyclopentadienes. New J. Chem., 49(20), 8442–8453. https://doi.org/10.1039/D5NJ01025J
23. Karaś, A. & Łapczuk, A. (2025). Computational model of the formation of novel nitronorbornene analogs via Diels–Alder process. React. Kinet. Mech. Catal., 138(4), 2671–2689. https://doi.org/10.1007/s11144-025-02869-1
24. Wróblewska, A., Sadowski, M. & Jasiński, R. (2024). Selectivity and molecular mechanism of the Au(III)-catalyzed [3+2] cycloaddition reaction between (Z)-C,N-diphenylnitrone and nitroethene in the light of the molecular electron density theory computational study. Chem. Heterocycl. Compd., 60(11–12), 639–645. https://doi.org/10.1007/s10593-025-03387-7
25. Kula, K. & Jasiński, R. (2024). Synthesis of bis(het)aryl systems via domino reaction involving (2E,4E)-2,5-dinitrohexa-2,4-diene: DFT mechanistic considerations. Chem. Heterocycl. Compd., 60(11–12), 600–610. https://doi.org/10.1007/s10593-025-03383-x
26. Aitouna, A.O., Syed, A., Alfagham, A.T., Mazoir, N., de Julián-Ortiz, J.V., Elgorban, A.M., Idrissi, M. El, Wong, L.S., Zeroual, A. (2024). Investigating the chemical reactivity and molecular docking of 2-diazo-3,3,3-trifluoro-1-nitropropane with phenyl methacrylate using computational methods. Chem. Heterocycl. Compd., 60(11–12), 592–599. https://doi.org/10.1007/s10593-025-03382-y
27. Ameur, S., Barhoumi, A., Abdallaoui, H.E.A. El, Syed, A., Belghiti, M.E., Elgorban, A.M., Wong, L.S., Wang, S., Idrissi, M. El, Zeroual, A., Mazoir, N. (2024). Molecular docking, exploring diverse selectivities and mechanistic insights in the cycloaddition reaction between 3-benzoylpyrrolo-[1,2-a]quinoxaline-1,2,4(5H)-triones and butyl vinyl ether. Chem. Heterocycl. Compd., 60(11–12), 584–591. https://doi.org/10.1007/s10593-025-03381-z
28. Westaway, K. C., Pham, T. Van & Fang, Y. (1997). Using Secondary α Deuterium Kinetic Isotope Effects To Determine the Symmetry of S N 2 Transition States. J. Am. Chem. Soc., 119(16), 3670–3676. https://doi.org/10.1021/ja962088f
29. Mao, Z. & Campbell, C. T. (2020). Kinetic Isotope Effects: Interpretation and Prediction Using Degrees of Rate Control. ACS Catal., 10(7), 4181–4192. https://doi.org/10.1021/acscatal.9b05637
30. Jasiński, R. (2016). A reexamination of the molecular mechanism of the Diels–Alder reaction between tetrafluoroethene and cyclopentadiene. React. Kinet. Mech. Catal., 119(1), 49–57. https://doi.org/10.1007/s11144-016-1038-1
31. Østergaard, L. F. & Hammerum, S. (2021). Secondary kinetic deuterium isotope effects on unimolecular cleavage reactions: Zero‐point vibrational energy and qualitative RRKM theory. Mass Spectrom. Rev., 40(6), 821–839. https://doi.org/10.1002/mas.21660
32. Storer, J. W., Raimondi, L. & Houk, K. N. (1994). Theoretical Secondary Kinetic Isotope Effects and the Interpretation of Transition State Geometries. 2. The Diels-Alder Reaction Transition State Geometry. J. Am. Chem. Soc., 116(21), 9675–9683. https://doi.org/10.1021/ja00100a037
33. Amyes, T. L. & Richard, J. P. (2017). Primary Deuterium Kinetic Isotope Effects From Product Yields: Rationale, Implementation, and Interpretationp. 163–177. https://doi.org/10.1016/bs.mie.2017.06.043
34. Simmons, E. M. & Hartwig, J. F. (2012). On the Interpretation of Deuterium Kinetic Isotope Effects in C-H Bond Functionalizations by Transition‐Metal Complexes. Angew. Chemie Int. Ed., 51(13), 3066–3072. https://doi.org/10.1002/anie.201107334
35. Koch, H. F., Dahlberg, D. B., McEntee, M. F. & Klecha, C. J. (1976). Use of kinetic isotope effects in mechanism studies. Anomalous Arrhenius parameters in the study of elimination reactions. J. Am. Chem. Soc., 98(4), 1060–1061. https://doi.org/10.1021/ja00420a055
36. Giagou, T. & Meyer, M. P. (2010). Kinetic Isotope Effects in Asymmetric Reactions. Chem. – A Eur. J., 16(35), 10616–10628. https://doi.org/10.1002/chem.201001018
37. Boguszewska-Czubara, A., Kula, K., Wnorowski, A., Biernasiuk, A., Popiołek, Ł., Miodowski, D., Demchuk, O.M., Jasiński, R. (2019). Novel functionalized β-nitrostyrenes: Promising candidates for new antibacterial drugs. Saudi Pharm. J., 27(4), 593–601. https://doi.org/10.1016/j.jsps.2019.02.007
38. Ramamoorthy, V., Ramasubbu, A., Muthusubramanian, S. & Sivasubramanian, S. (1999). Pillared Buserite as a new catalytic material for the 1,3-dipolar cycloaddition of α-phenyl-N-(p-methyphenyl) nitrone with electron deficient olefins. Synth. Commun., 29(1), 21–26. https://doi.org/10.1080/00397919908085730
39. Banerji, A., Gupta, M., Biswas, P. K., Prangé, T. & Neuman, A. (2007). 1,3‐dipolar cycloadditions. Part XII ‐ selective cycloaddition route to 4‐nitroisoxazolidine ring systems. J. Heterocycl. Chem., 44(5), 1045–1049. https://doi.org/10.1002/jhet.5570440511
40. Joucla, M., Grée, D. & Hamelin, J. (1973). Cycloaddition dipolaire 1,3 sur des composes a liaison ethylenique activee—XVII. Tetrahedron, 29(15), 2315–2322. https://doi.org/10.1016/S0040-4020(01)93355-1
41. Jasiński, R. (2004). Reakcje [2+3] cykloaddycji Z-C,N-difenylonitronu i C,C,N-trifenylonitronu ze sprzężonymi nitroalkenami. Politechnika Krakowska.
42. Roothaan, C. C. J. (1951). New Developments in Molecular Orbital Theory. Rev. Mod. Phys., 23(2), 69–89. https://doi.org/10.1103/RevModPhys.23.69
43. Lee, C., Yang, W. & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B, 37(2), 785–789. https://doi.org/10.1103/PhysRevB.37.785
44. Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys., 98(7), 5648–5652. https://doi.org/10.1063/1.464913
45. Becke, A. D. (1997). Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals. J. Chem. Phys., 107(20), 8554–8560. https://doi.org/10.1063/1.475007
46. Chai, J.-D. Da & Head-Gordon, M. (2008). Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Phys. Chem. Chem. Phys, 10(44), 6615. https://doi.org/10.1039/b810189b
47. Zhao, Y. & Truhlar, D. G. (2008). The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other function. Theor. Chem. Acc., 120(1–3), 215–241. https://doi.org/10.1007/s00214-007-0310-x
48. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J (2016). Gaussian 16, Revision A.03. Gaussian Inc. Wallingford CT.
49. Cossi, M., Rega, N., Scalmani, G. & Barone, V. (2003). Energies, structures, and electronic properties of molecules in solution with the C‐PCM solvation model. J. Comput. Chem., 24(6), 669–681. https://doi.org/10.1002/jcc.10189
50. Laidler, K. J. (1987). Chemical Kinetics. 3rd Edition. Singapore City: Pearson Education.
2. Domingo, L. R., Kula, K., Ríos-Gutiérrez, M. & Jasiński, R. (2021). Understanding the Participation of Fluorinated Azomethine Ylides in Carbenoid-Type [3 + 2] Cycloaddition Reactions with Ynal Systems: A Molecular Electron Density Theory Study. J. Org. Chem., 86(18), 12644–12653. https://doi.org/10.1021/acs.joc.1c01126
3. Sadowski, M. (2024). Alternative Synthetic Protocols as a Way to Mask Unreliability in Organic Chemistry Research, Case of Nitrones. Sci. Radices, 3(4), 287–293. https://doi.org/10.58332/scirad2024v3i4a05
4. Kang, P.-L. & Liu, Z.-P. (2021). Reaction prediction via atomistic simulation: from quantum mechanics to machine learning. iScience, 24(1), 102013. https://doi.org/10.1016/j.isci.2020.102013
5. Łapczuk-Krygier, A., Ponikiewski, Ł. & Jasiński, R. (2014). The crystal structure of (1RS,4RS,5RS,6SR)-5-cyano-5-nitro-6-phenyl-bicyclo[2.2.1]hept-2-ene. Crystallogr. Rep., 59(7), 961–963. https://doi.org/10.1134/S1063774514070128
6. Takahashi, J. (2023). X-Rays (Organic Synthesis). In Encyclopedia of Astrobiologyp. 3253–3254. Berlin, Heidelberg: Springer Berlin Heidelberg. https://doi.org/10.1007/978-3-662-65093-6_1696
7. Gillies, J. Z., Gillies, C. W., Lovas, F. J., Matsumura, K., Suenram, R. D., Kraka, E. & Cremer, D. (1991). Van der Waals complexes of chemically reactive gases: ozone-acetylene. J. Am. Chem. Soc., 113(17), 6408–6415. https://doi.org/10.1021/ja00017a008
8. Gillies, C. W., Gillies, J. Z., Suenram, R. D., Lovas, F. J., Kraka, E. & Cremer, D. (1991). Van der Waals complexes in 1,3-dipolar cycloaddition reactions: ozone-ethylene. J. Am. Chem. Soc., 113(7), 2412–2421. https://doi.org/10.1021/ja00007a010
9. Weisenburger, G.A., Barnhart, R.W., Clark, J.D., Dale, D.J., Hawksworth, M., Higginson, P.D., Kang, Y., Knoechel, D.J., Moon, B.S., Shaw, S.M., Taber G.P., Tickner, D. L. (2007). Determination of Reaction Heat: A Comparison of Measurement and Estimation Techniques. Org. Process Res. Dev, 11(6), 1112–1125. https://doi.org/10.1021/op700173h
10. Jasiński, R. (2015). In the searching for zwitterionic intermediates on reaction paths of [3 + 2] cycloaddition reactions between 2,2,4,4-tetramethyl-3-thiocyclobutanone S-methylide and polymerizable olefins. RSC Adv., 5(122), 101045–101048. https://doi.org/10.1039/C5RA20747A
11. Suresh, L., Lalrempuia, R., Fjermestad, T., Törnroos, K.W., Bour, J., Frache, G., Nova, A., Le Roux, E. (2025). Trapping of Key “Ate” Intermediates of NHC-Group IV Relevant to Catalyzing Copolymerization of Cyclohexene Oxide with CO 2. Organometallics, 44(1), 68–81. https://doi.org/10.1021/acs.organomet.4c00371
12. Amano, F., Nakayama, S., Suzuki, S., Yamakata, A. & Beppu, K. (2024). Trapping of Intermediates of a Photocatalytic Oxygen Evolution Reaction in Overall Water Splitting. ACS Appl. Energy Mater., 7(4), 1398–1402. https://doi.org/10.1021/acsaem.3c03172
13. Jodłowski, P.J., Chlebda, D., Piwowarczyk, E., Chrzan, M., Jędrzejczyk, R.J., Sitarz, M., Węgrzynowicz, A., Kołodziej, A., Łojewska, J. (2016). In situ and operando spectroscopic studies of sonically aided catalysts for biogas exhaust abatement. J. Mol. Struct., 1126, 132–140. https://doi.org/10.1016/j.molstruc.2016.02.039
14. Ronduda, H., Zybert, M., Patkowski, W., Ostrowski, A., Jodłowski, P., Szymański, D., Kępiński, L., Raróg-Pilecka, W. (2021). A high performance barium-promoted cobalt catalyst supported on magnesium–lanthanum mixed oxide for ammonia synthesis. RSC Adv., 11(23), 14218–14228. https://doi.org/10.1039/D1RA01584B
15. Jodłowski, P. J., Kurowski, G., Dymek, K., Oszajca, M., Piskorz, W., Hyjek, K., … Sitarz, M. (2023). From crystal phase mixture to pure metal-organic frameworks – Tuning pore and structure properties. Ultrason. Sonochem., 95, 106377. https://doi.org/10.1016/j.ultsonch.2023.106377
16. Polanyi, J. C. & Zewail, A. H. (1995). Direct Observation of the Transition State. Acc. Chem. Res., 28(3), 119–132. https://doi.org/10.1021/ar00051a005
17. Maiuri, M., Garavelli, M. & Cerullo, G. (2020). Ultrafast Spectroscopy: State of the Art and Open Challenges. J. Am. Chem. Soc., 142(1), 3–15. https://doi.org/10.1021/jacs.9b10533
18. Eyring, H. (1935). The Activated Complex in Chemical Reactions. J. Chem. Phys., 3(2), 107–115. https://doi.org/10.1063/1.1749604
19. Zawadzińska-Wrochniak, K., Kula, K., Ríos-Gutiérrez, M., Gostyński, B., Krawczyk, T. & Jasiński, R. (2025). A Comprehensive Study of the Synthesis, Spectral Characteristics, Quantum–Chemical Molecular Electron Density Theory, and In Silico Future Perspective of Novel CBr3-Functionalyzed Nitro-2-Isoxazolines Obtained via (3 + 2) Cycloaddition of (E)-3,3,3-Tribro. Molecules, 30(10), 2149. https://doi.org/10.3390/molecules30102149
20. Sadowski, M., Dresler, E. & Jasiński, R. (2025). On the Question of the Regio-Orientation, Stereo-Orientation and Molecular Mechanism in the Cascade Cycloaddition/Rearrangement/Elimination Processes Leading to Nitro-Substituted Thiopyran Analogs: DFT Computational Study. Int. J. Mol. Sci., 26(18), 8948. https://doi.org/10.3390/ijms26188948
21. Kącka‐Zych, A., Zeroual, A., Syed, A. & Bahkali, A. H. (2025). Docking Survey, ADME , Toxicological Insights, and Mechanistic Exploration of the Diels–Alder Reaction Between Hexachlorocyclopentadiene and Dichloroethylene. J. Comput. Chem., 46(10). https://doi.org/10.1002/jcc.70092
22. Woliński, P., Dresler, E. & Jasiński, R. (2025). A new mechanistic insight into the molecular mechanisms of the addition reactions of 2-aryl-3-nitro-2 H -chromenes to pyrazoles and cyclopentadienes. New J. Chem., 49(20), 8442–8453. https://doi.org/10.1039/D5NJ01025J
23. Karaś, A. & Łapczuk, A. (2025). Computational model of the formation of novel nitronorbornene analogs via Diels–Alder process. React. Kinet. Mech. Catal., 138(4), 2671–2689. https://doi.org/10.1007/s11144-025-02869-1
24. Wróblewska, A., Sadowski, M. & Jasiński, R. (2024). Selectivity and molecular mechanism of the Au(III)-catalyzed [3+2] cycloaddition reaction between (Z)-C,N-diphenylnitrone and nitroethene in the light of the molecular electron density theory computational study. Chem. Heterocycl. Compd., 60(11–12), 639–645. https://doi.org/10.1007/s10593-025-03387-7
25. Kula, K. & Jasiński, R. (2024). Synthesis of bis(het)aryl systems via domino reaction involving (2E,4E)-2,5-dinitrohexa-2,4-diene: DFT mechanistic considerations. Chem. Heterocycl. Compd., 60(11–12), 600–610. https://doi.org/10.1007/s10593-025-03383-x
26. Aitouna, A.O., Syed, A., Alfagham, A.T., Mazoir, N., de Julián-Ortiz, J.V., Elgorban, A.M., Idrissi, M. El, Wong, L.S., Zeroual, A. (2024). Investigating the chemical reactivity and molecular docking of 2-diazo-3,3,3-trifluoro-1-nitropropane with phenyl methacrylate using computational methods. Chem. Heterocycl. Compd., 60(11–12), 592–599. https://doi.org/10.1007/s10593-025-03382-y
27. Ameur, S., Barhoumi, A., Abdallaoui, H.E.A. El, Syed, A., Belghiti, M.E., Elgorban, A.M., Wong, L.S., Wang, S., Idrissi, M. El, Zeroual, A., Mazoir, N. (2024). Molecular docking, exploring diverse selectivities and mechanistic insights in the cycloaddition reaction between 3-benzoylpyrrolo-[1,2-a]quinoxaline-1,2,4(5H)-triones and butyl vinyl ether. Chem. Heterocycl. Compd., 60(11–12), 584–591. https://doi.org/10.1007/s10593-025-03381-z
28. Westaway, K. C., Pham, T. Van & Fang, Y. (1997). Using Secondary α Deuterium Kinetic Isotope Effects To Determine the Symmetry of S N 2 Transition States. J. Am. Chem. Soc., 119(16), 3670–3676. https://doi.org/10.1021/ja962088f
29. Mao, Z. & Campbell, C. T. (2020). Kinetic Isotope Effects: Interpretation and Prediction Using Degrees of Rate Control. ACS Catal., 10(7), 4181–4192. https://doi.org/10.1021/acscatal.9b05637
30. Jasiński, R. (2016). A reexamination of the molecular mechanism of the Diels–Alder reaction between tetrafluoroethene and cyclopentadiene. React. Kinet. Mech. Catal., 119(1), 49–57. https://doi.org/10.1007/s11144-016-1038-1
31. Østergaard, L. F. & Hammerum, S. (2021). Secondary kinetic deuterium isotope effects on unimolecular cleavage reactions: Zero‐point vibrational energy and qualitative RRKM theory. Mass Spectrom. Rev., 40(6), 821–839. https://doi.org/10.1002/mas.21660
32. Storer, J. W., Raimondi, L. & Houk, K. N. (1994). Theoretical Secondary Kinetic Isotope Effects and the Interpretation of Transition State Geometries. 2. The Diels-Alder Reaction Transition State Geometry. J. Am. Chem. Soc., 116(21), 9675–9683. https://doi.org/10.1021/ja00100a037
33. Amyes, T. L. & Richard, J. P. (2017). Primary Deuterium Kinetic Isotope Effects From Product Yields: Rationale, Implementation, and Interpretationp. 163–177. https://doi.org/10.1016/bs.mie.2017.06.043
34. Simmons, E. M. & Hartwig, J. F. (2012). On the Interpretation of Deuterium Kinetic Isotope Effects in C-H Bond Functionalizations by Transition‐Metal Complexes. Angew. Chemie Int. Ed., 51(13), 3066–3072. https://doi.org/10.1002/anie.201107334
35. Koch, H. F., Dahlberg, D. B., McEntee, M. F. & Klecha, C. J. (1976). Use of kinetic isotope effects in mechanism studies. Anomalous Arrhenius parameters in the study of elimination reactions. J. Am. Chem. Soc., 98(4), 1060–1061. https://doi.org/10.1021/ja00420a055
36. Giagou, T. & Meyer, M. P. (2010). Kinetic Isotope Effects in Asymmetric Reactions. Chem. – A Eur. J., 16(35), 10616–10628. https://doi.org/10.1002/chem.201001018
37. Boguszewska-Czubara, A., Kula, K., Wnorowski, A., Biernasiuk, A., Popiołek, Ł., Miodowski, D., Demchuk, O.M., Jasiński, R. (2019). Novel functionalized β-nitrostyrenes: Promising candidates for new antibacterial drugs. Saudi Pharm. J., 27(4), 593–601. https://doi.org/10.1016/j.jsps.2019.02.007
38. Ramamoorthy, V., Ramasubbu, A., Muthusubramanian, S. & Sivasubramanian, S. (1999). Pillared Buserite as a new catalytic material for the 1,3-dipolar cycloaddition of α-phenyl-N-(p-methyphenyl) nitrone with electron deficient olefins. Synth. Commun., 29(1), 21–26. https://doi.org/10.1080/00397919908085730
39. Banerji, A., Gupta, M., Biswas, P. K., Prangé, T. & Neuman, A. (2007). 1,3‐dipolar cycloadditions. Part XII ‐ selective cycloaddition route to 4‐nitroisoxazolidine ring systems. J. Heterocycl. Chem., 44(5), 1045–1049. https://doi.org/10.1002/jhet.5570440511
40. Joucla, M., Grée, D. & Hamelin, J. (1973). Cycloaddition dipolaire 1,3 sur des composes a liaison ethylenique activee—XVII. Tetrahedron, 29(15), 2315–2322. https://doi.org/10.1016/S0040-4020(01)93355-1
41. Jasiński, R. (2004). Reakcje [2+3] cykloaddycji Z-C,N-difenylonitronu i C,C,N-trifenylonitronu ze sprzężonymi nitroalkenami. Politechnika Krakowska.
42. Roothaan, C. C. J. (1951). New Developments in Molecular Orbital Theory. Rev. Mod. Phys., 23(2), 69–89. https://doi.org/10.1103/RevModPhys.23.69
43. Lee, C., Yang, W. & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B, 37(2), 785–789. https://doi.org/10.1103/PhysRevB.37.785
44. Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys., 98(7), 5648–5652. https://doi.org/10.1063/1.464913
45. Becke, A. D. (1997). Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals. J. Chem. Phys., 107(20), 8554–8560. https://doi.org/10.1063/1.475007
46. Chai, J.-D. Da & Head-Gordon, M. (2008). Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Phys. Chem. Chem. Phys, 10(44), 6615. https://doi.org/10.1039/b810189b
47. Zhao, Y. & Truhlar, D. G. (2008). The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other function. Theor. Chem. Acc., 120(1–3), 215–241. https://doi.org/10.1007/s00214-007-0310-x
48. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J (2016). Gaussian 16, Revision A.03. Gaussian Inc. Wallingford CT.
49. Cossi, M., Rega, N., Scalmani, G. & Barone, V. (2003). Energies, structures, and electronic properties of molecules in solution with the C‐PCM solvation model. J. Comput. Chem., 24(6), 669–681. https://doi.org/10.1002/jcc.10189
50. Laidler, K. J. (1987). Chemical Kinetics. 3rd Edition. Singapore City: Pearson Education.