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 title Project leader Project code Project type Cikloadicijske strategije prema policikličkim gvanidinima-CycloGu Davor Margetić IP-2018-01-3298 HRZZ
Depositing User:	Zoran Glasovac
Date Deposited:	27 Dec 2019 11:02
URI:	http://fulir.irb.hr/id/eprint/5282
DOI:	10.5562/cca3570

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