Five-Membered Heterocycles. Part V. Impact of Heteroatoms on Aromaticity of Five-Membered Heterocycles

• Autorzy: Mrozek A. , Karolak-Wojciechowska J.
• Języki publikacji: EN

Abstrakty

EN

The aromaticity (in the form ofHOMAindex) of various five-membered heterorings systems and their bicyclic derivatives containing N, S, O, and P were studied on the basis of statistical data from Cambridge Structural Database (CSD). The calculations of HOMA were done for pyrroles, furans, thiophenes, phospholes, imidazoles, oxazoles, thiazoles, phosphazoles as well as for 6 + 5 fused systems: benzimidazoles, benzoxazoles, benzothiazoles, and benzophosphazoles. Detailed analysis showed that relationship between classical aromaticity and electronegativity of heteroatom is described by squared equation. An optimal value of electronegativity is about 2.9 (Pauling’s scale) for which aromaticity of heterorings reaches the highest level. For fused systems, the presence of benzene ring causes the evident increasing of average value of HOMA indices.

Słowa kluczowe

EN

heteroaromaticity; electronegativity; HOMA; CSD

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 5-6
• Strony: 721--730
• Opis fizyczny: Bibliogr. 27 poz., rys.

Twórcy

autor

Mrozek A.

autor

Karolak-Wojciechowska J.

• Institute of General and Ecological Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland,

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