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Izvorni znanstveni članak
https://doi.org/10.5562/cca3570
Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes
Ivana Antol
; Laboratory for physical organic chemistry, Division of organic chemistry and biochemistry, Ruđer Bošković Institute, Zagreb, Croatia
Luka Barešić
; Laboratory for physical organic chemistry, Division of organic chemistry and biochemistry, Ruđer Bošković Institute, Zagreb, Croatia
Zoran Glasovac
; Laboratory for physical organic chemistry, Division of organic chemistry and biochemistry, Ruđer Bošković Institute, Zagreb, Croatia
Davor Margetić
; Laboratory for physical organic chemistry, Division of organic chemistry and biochemistry, Ruđer Bošković Institute, Zagreb, Croatia
| Puni tekst: engleski, pdf (8 MB) | str. 279-286 | citiraj | |
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APA 6th Edition Antol, I., Barešić, L., Glasovac, Z. i Margetić, D. (2019). Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes. Croatica Chemica Acta, 92 (2), 279-286. https://doi.org/10.5562/cca3570 MLA 8th Edition Antol, Ivana, et al. "Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes." Croatica Chemica Acta, vol. 92, br. 2, 2019, str. 279-286. https://doi.org/10.5562/cca3570. Citirano 05.03.2021. Chicago 17th Edition Antol, Ivana, Luka Barešić, Zoran Glasovac i Davor Margetić. "Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes." Croatica Chemica Acta 92, br. 2 (2019): 279-286. https://doi.org/10.5562/cca3570 Harvard Antol, I., et al. (2019). 'Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes', Croatica Chemica Acta, 92(2), str. 279-286. https://doi.org/10.5562/cca3570 Vancouver Antol I, Barešić L, Glasovac Z, Margetić D. Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes. Croatica Chemica Acta [Internet]. 2019 [pristupljeno 05.03.2021.];92(2):279-286. https://doi.org/10.5562/cca3570 IEEE I. Antol, L. Barešić, Z. Glasovac i D. Margetić, "Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes", Croatica Chemica Acta, vol.92, br. 2, str. 279-286, 2019. [Online]. https://doi.org/10.5562/cca3570 |
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Sažetak
Quantum-chemical calculations of cycloaddition properties of cyclic heterodienes substituted with guanidine functionality were carried out. Molecular and electronic structures of series of dienes (pyrrole, furan, thiophene, isoindole and 1,3-butadiene) were calculated and reactivity order established on the basis of FMO theory. Transition state calculations of model [4+2] cycloaddition reaction with acetylene indicate that guanidine substitution influences reaction barriers in moderate extent (up to ~4 kcal mol–1). The substitution position plays an important role on the sign and magnitude of the effect and protonation of nitrogen possessing substituents increases reactivity of dienes.
This work is licensed under a Creative Commons Attribution 4.0 International License.
Ključne riječi
heterocyclic chemistry; cycloaddition reactions; guanidines; organic chemistry; calculations
Hrčak ID: 227083
URI
https://hrcak.srce.hr/227083
Moj profil
Srce