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
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
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.