On the influence of spiroconjugation and electron-withdrawing effects on the Frontier orbital energies of 5-substituted cyclopentadienes

Autor:	J.Venkat Raman, Gary I. Dmitrienko, Luke A. Burke, Kent E. Nielsen, Leslie H. Randall
Rok vydání:	1994
Předmět:	chemistry.chemical_compound Cyclopentadiene chemistry Nitrile Computational chemistry Ab initio quantum chemistry methods Organic Chemistry Drug Discovery Polar effect Electronic structure Perturbation theory Biochemistry HOMO/LUMO
Zdroj:	Tetrahedron Letters. 35:5973-5976
ISSN:	0040-4039
DOI:	10.1016/0040-4039(94)88052-2
Popis:	Ab initio calculations reveal that the influence of spiroconjugation on the HOMO of 5-substituted cyclopentadienes is weak relative to electron withdrawing effects and that both the HOMO and LUMO energy levels can be lower than in cyclopentadiene contrary to the predictions of qualitative perturbation theory. In accord with these theoretical results, the reaction of 5,5-dicyanocyclopentadiene with cyclopentadiene yields only heterodimers.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b03b718cb8d2376db732ee1718df387f https://doi.org/10.1016/0040-4039(94)88052-2 Zobrazit plný text záznamu