Naslov
Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes

Autori
Antol, Ivana ; Barešić, Luka ; Glasovac, Zoran ; Margetić, Davor

Izvornik
Croatica chemica acta (0011-1643) 92 (2019), 2; 279-286

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
heterocyclic chemistry ; cycloaddition reactions ; guanidines ; organic chemistry ; calculations

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA