Sterical index: a novel, simple tool for the interpretation of organic reaction mechanisms

• Autorzy: Dresler Ewa , Allnajar Radwan , Jasiński Radomir

Identyfikatory

DOI

10.58332/scirad2023v2i1a06

• Języki publikacji: EN

Abstrakty

EN

A new, simple index for the quantitative description of steric effects was proposed based on the results of DFT calculations. This effect was connected with the disturbance of synchronicity within transition states of the model Diels-Alder reaction. The obtained results offer the possibility of predicting steric effects determined by alkyl groups for a wide range of bimolecular processes.

Słowa kluczowe

EN

organic reactivity; steric effect; cycloaddition

PL

reaktywność organiczna; efekt steryczny; cykloaddycja

• Wydawca: Radomskie Towarzystwo Naukowe
• Czasopismo: Scientiae Radices
• Rocznik: 2023
• Tom: Vol. 2, Iss. 1
• Strony: 69--74
• Opis fizyczny: Bibliogr. 11 poz., il. (w tym 1 kolor.), rys.

Twórcy

autor

Dresler Ewa

• Łukasiewicz Research Network - Institute of Heavy Organic Synthesis “Blachownia” Energetyków 9, 47-225 Kędzierzyn-Koźle, Poland

autor

Allnajar Radwan

• Department of Chemistry, Faculty of Science, University of Benghazi, Benghazi, Libya

autor

Jasiński Radomir

• PharmD, Faculty of Pharmacy, Libyan International Medical University, Benghazi, Libya

Bibliografia

• [1] Domingo, L.R.; Ríos-Gutiérrez, M.; Pérez, P.; Applications of the conceptual density functional indices to organic chemistry reactivity. Molecules 2016, 21, 748. DOI: 10.3390/molecules21060748
• [2] Domingo, L.R.; Chamorro, E.; Pérez, P.; An Analysis of the Regioselectivity of 1,3-Dipolar Cycloaddition Reactions of Benzonitrile N-Oxides Based on Global and Local Electrophilicity and Nucleophilicity Indices. Eur. J. Org. Chem. 2009, 3036-3044. DOI: 10.1002/ejoc.200900213
• [3] Chandra, A.K.; Nguyen, M.T.; Use of Local Softness for the Interpretation of Reaction Mechanisms. Int. J. Mol. Sci. 2002, 3, 310-323. DOI: 10.3390/i3040310
• [4] Cárdenas-Jirón, G.I.; Gutiérrez-Oliva, S.; Melin, J.; Toro-Labbé, A.; Relations between Potential Energy, Electronic Chemical Potential, and Hardness Profiles. J. Phys. Chem. A 1997, 101, 4621-4627. DOI: 10.1021/jp9638705
• [5] Sauer, J.; Sustmann, R.; Mechanistic Aspects of Diels-Alder Reactions: A Critical Survey. Angew. Chem. 1980, 19, 779-807. DOI:10.1002/anie.198007791
• [6] Nicolaou, K.C.; Snyder, S.A.; Montagnon, T.; Vassilikogiannakis, G.; The Diels-Alder Reaction in Total Synthesis. Angew. Chem. 2002, 41, 1668-1698. DOI: 10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z
• [7] Domingo, L.R.; Sáez, J.A.; Understanding the mechanism of polar Diels-Alder reactions Org. Biomol. Chem. 2009, 7, 3576-3583. DOI: 10.1039/b909611f
• [8] Domingo, L.R.; Aurell, M.J.; Pérez, P.; A DFT analysis of the participation of zwitterionic TACs in polar [3+2] cycloaddition reactions, Tetrahedron, 2014, 70, 4519-4525. DOI: 10.1016/j.tet.2014.05.003
• [9] Jasiński, R.; β-Trifluoromethylated nitroethenes in Diels-Alder reaction with cyclopentadiene: A DFT computational study. J. Fluor. Chem. 2018, 206, 1-7. DOI: 10.1016/j.jfluchem.2017.12.008.
• [10] Kula, K.; Łapczuk-Krygier, A.; A DFT computational study on the [3+2] cycloaddition between parent thionitrone and nitroethene. Curr. Chem. Lett. 2018, 7, 27-34. DOI: 10.5267/j.ccl.2018.02.001
• [11] Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.P.; Izmaylov, A.F.; Bloino, J.; Zheng, G.; Sonnenberg, J.L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.;. Nakai, H.; Vreven, T.; Montgomery, J.A.; Jr., Peralta, J.E.; Ogliaro, F.; Bearpark, M.; Heyd, J.J.; Brothers, E.; Kudin, K.N.; Staroverov, V.N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J.C.; Iyengar, S.S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J.M.; Klene, M.; Knox, J.E.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Martin, L.R.; Morokuma, K.; Zakrzewski, V.G.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Dap-prich, S.; Daniels, A.D.; Farkas, Ö.; Foresman, J.B.; Ortiz, J.V.; Cioslowski, J.; Fox, D.J. Gaussian 09 (Gaussian, Inc., Wallingford CT, 2009).

Uwagi

W artykule podane również dwie nieprzypisane do autorów afiliacje: Radom Scientific Society, Rynek 15, 26-600 Radom, Poland oraz Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow, Poland.

Opracowanie rekordu ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023).