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

Antol, Ivana; Barešić, Luka; Glasovac, Zoran; Margetić, Davor (2019) Computational Study of Electronic Influence of Guanidine Substitution on Diels-Alder Reactions of Heterocyclic Dienes. Croatica Chemica Acta, 92 (2). pp. 279-286. ISSN 0011-1643

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: heterocyclic chemistry ; cycloaddition reactions ; guanidines ; organic chemistry ; calculations
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Cikloadicijske strategije prema policikličkim gvanidinima-CycloGuDavor MargetićIP-2018-01-3298HRZZ
Depositing User: Zoran Glasovac
Date Deposited: 27 Dec 2019 11:02
Last Modified: 23 Apr 2020 10:17
URI: http://fulir.irb.hr/id/eprint/5282
DOI: 10.5562/cca3570

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