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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 preuzimanja: 76* citiraj
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 29.02.2020.
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 29.02.2020.];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

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.

Creative Commons License 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

Posjeta: 143 *