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Ab initio and Semiempirical Modelling of Stereoselectivities of Diels-Alder Cycloadditions of Furan and Cyclopentadiene with Norbornenes

Davor Margetić ; Laboratory for Physical Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, 10002 Zagreb, Croatia
Ronald N. Warrener ; Centre for Molecular Architecture, Central Queensland University, North Rockhampton, 4702, QLD, Australia

Puni tekst: engleski, pdf (283 KB) str. 357-363 preuzimanja: 309* citiraj
APA 6th Edition
Margetić, D. i Warrener, R.N. (2003). Ab initio and Semiempirical Modelling of Stereoselectivities of Diels-Alder Cycloadditions of Furan and Cyclopentadiene with Norbornenes. Croatica Chemica Acta, 76 (4), 357-363. Preuzeto s https://hrcak.srce.hr/103199
MLA 8th Edition
Margetić, Davor i Ronald N. Warrener. "Ab initio and Semiempirical Modelling of Stereoselectivities of Diels-Alder Cycloadditions of Furan and Cyclopentadiene with Norbornenes." Croatica Chemica Acta, vol. 76, br. 4, 2003, str. 357-363. https://hrcak.srce.hr/103199. Citirano 27.10.2021.
Chicago 17th Edition
Margetić, Davor i Ronald N. Warrener. "Ab initio and Semiempirical Modelling of Stereoselectivities of Diels-Alder Cycloadditions of Furan and Cyclopentadiene with Norbornenes." Croatica Chemica Acta 76, br. 4 (2003): 357-363. https://hrcak.srce.hr/103199
Harvard
Margetić, D., i Warrener, R.N. (2003). 'Ab initio and Semiempirical Modelling of Stereoselectivities of Diels-Alder Cycloadditions of Furan and Cyclopentadiene with Norbornenes', Croatica Chemica Acta, 76(4), str. 357-363. Preuzeto s: https://hrcak.srce.hr/103199 (Datum pristupa: 27.10.2021.)
Vancouver
Margetić D, Warrener RN. Ab initio and Semiempirical Modelling of Stereoselectivities of Diels-Alder Cycloadditions of Furan and Cyclopentadiene with Norbornenes. Croatica Chemica Acta [Internet]. 2003 [pristupljeno 27.10.2021.];76(4):357-363. Dostupno na: https://hrcak.srce.hr/103199
IEEE
D. Margetić i R.N. Warrener, "Ab initio and Semiempirical Modelling of Stereoselectivities of Diels-Alder Cycloadditions of Furan and Cyclopentadiene with Norbornenes", Croatica Chemica Acta, vol.76, br. 4, str. 357-363, 2003. [Online]. Dostupno na: https://hrcak.srce.hr/103199. [Citirano: 27.10.2021.]

Sažetak
Ab initio (RHF/3-21G and RHF/6-31G* basis sets) and semiempirical (AM1 and PM3) quantum chemical calculations have been applied to a study of Diels-Alder reactions of furan and cyclopentadiene as 1,3-dienes, with norbornene and 7-oxanorbornene as dienophiles, in order to model π-facial selectivities and stereoselectivities of these reactions. To achieve this goal, transition states for these reactions are located and activation energies estimated. The exclusive exo π-facial selectivity exhibited in these cycloadditions are readily predicted using semiempirical or ab initio methods. To determine stereochemical outcomes following π-facial attack, ab initio calculations are required. Exo,endo stereoselectivities found experimentally, are successfully predicted by using RHF/6-31G*//3-21G or higher levels of calculations. Secondary orbital interactions are postulated to be responsible for the experimental stereoselectivities.

Ključne riječi
ab initio calculations; semiempirical calculations; cycloadditions; Diels-Alder reaction; dienes

Hrčak ID: 103199

URI
https://hrcak.srce.hr/103199

Posjeta: 518 *