Asymmetric p(O)-pi(Triazine) Conjugation in the Formally Symmetric Bis(4,6-dimethoxy-1,3,5-triazinyl) Ether in Its Crystal Structure

• Autorzy: Główka M. L. , Błaszczyk M. , Olczak A. , Kamińska J. E. , Kamiński Z. J.
• Języki publikacji: EN

Abstrakty

EN

Reported is the crystal structure of a formally symmetric bis(s-triazinyl) ether obtained as a by-product in the acylation reaction of less reactive nucleophiles with 2-acyloxy-4,6-dimethoxy-1,3,5-tri azines. The title ether shows conformational asymmetry evi - denced by different orientations of the four methoxy groups and the two aromatic rings in relation to the central etheric plane. Differentiation of the two O–C(triazine) bond lengths of the bis(triazinyl) ether can be correlated with the angles between s-triazine rings with the central etheric plane, indicating different degree of conjugation of the two pi-systems with alone pair of the central oxygen atom. It seems that primary reason for the observed asymmetry is crystal packing, causing different orientations of methoxy groups, which in turn induced bond lengths alternation in the s-triazine rings affecting their conjugations with central O atom through AGIBA effect. The experimental obser - vations are in agreement with ab in itio calculation.

Słowa kluczowe

EN

bis(s-triazinyl) ether; asymmetric conjugation; crystallographic asymmetry of symmetric ethers; AGIBA effect

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 12
• Strony: 2163--2172
• Opis fizyczny: Bibliogr. 28 poz., rys.

Twórcy

autor

Główka M. L.

autor

Błaszczyk M.

autor

Olczak A.

autor

Kamińska J. E.

autor

Kamiński Z. J.

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

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