MNDO study of the (anti)aromaticity of fluorine-containing cyclopentadienyl, indenyl, and cyclopenta[b]naphthyl cations

MNDO study of the (anti)aromaticity of fluorine-containing cyclopentadienyl, indenyl, and cyclopenta[b]naphthyl cations Научная публикация

Журнал

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Вых. Данные

Год: 2002, Том: 38, Номер: 7, Страницы: 995-1000 Страниц : 6 DOI: 10.1023/A:1020849528372

Авторы

Shchegoleva LN ¹ , Karpov VM ¹ , Platonov VE ¹

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Div, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

MNDO calculations were performed to estimate the aromaticity (antiaromaticity) of a series of fluorine-containing cyclopentadienyl, indenyl, and cyclopenta[b]naphthyl cations in terms of the Dewar-Breslow criterion which utilizes the difference in the enthalpies of formation of isomeric cations with closed and open pi-systems as aromaticity index. The aromaticity is strongly determined by both the structure of the carbon skeleton and the number and position of fluorine atoms. A linear correlation was revealed between the aromaticity index and the energy of the lowest singlet-singlet excitation for cations having a cyclic pi-system.

Shchegoleva L. , Karpov V. , Platonov V.
MNDO study of the (anti)aromaticity of fluorine-containing cyclopentadienyl, indenyl, and cyclopenta[b]naphthyl cations
Russian Journal of Organic Chemistry. 2002. V.38. N7. P.995-1000. DOI: 10.1023/A:1020849528372 WOS Scopus РИНЦ

Web of science	WOS:000179627200007
Scopus	2-s2.0-0036413729
РИНЦ	13395598
OpenAlex	W34291156