%0 Journal Article
%T Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes
%A Antol
%A Ivana
%A Bare£¿i£¿
%A Luka
%A Glasovac
%A Zoran
%A Margeti£¿
%A Davor
%J -
%D 2019
%R 10.5562/cca3570
%X Sa£¿etak 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¨C1). 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
%K heterocyclic chemistry
%K cycloaddition reactions
%K guanidines
%K organic chemistry
%K calculations
%U https://hrcak.srce.hr/index.php?show=clanak&id_clanak_jezik=330674