Bromlu fenstatin türevlerinin seryum (IV) amonyum nitrat/lityum bromür (CAN/LiBr) ile sentezi ve yoğunluk fonksiyonel teorisi (DFT) ile incelenmesi

Synthesis of brominated phenstatin derivatives via cerium (IV) ammonium nitrate / lithium bromide (CAN/LiBr) and investigation with the density functional theory (DFT)

Özet

Bu çalışmada, Eaton reaktifi (CH3SO3H/P2O5) kullanılarak fenstatin türevi olan (3,4-dimetoksifenil)(3,4,5- trimetoksifenil)metanon (7) sentezlendi. Diarilmetanon 7’nin seryum (IV) amonyum nitrat (CAN/LiBr) kullanılarak bromlanması ile (2-brom-3,4,5-trimetoksifenil)(3,4-dimetoksifenil)metanon (10) ve (2,6-dibrom-3,4,5- trimetoksifenil) (3,4-dimetoksifenil)metanon (11) sentezlendi. Sentezlenen bileşiklerin yapıları IR, HRMS, 1H ve 13C NMR spektroskopisi ile aydınlatıldı. Bileşiklerin geometrik parametreleri GAUSSIAN 09W paket programı kullanılarak, yoğunluk fonksiyonel teorisi (DFT) B3LYP/6-311G(d,p) metodu ile optimize edildi ve yapısal parametreleri (bağ açıları, bağ uzunlukları ve dihedral açıları) incelendi.

Abstract

In this study, (3,4-dimethoxyphenyl) (3,4,5-trimethoxyphenyl) methanone (7) being phenstatin derivation was synthesized using Eaton's reagent (CH3SO3H/P2O5). Novel compound (2-bromo-3,4,5-trimethoxyphenyl) (3,4- dimethoxyphenyl) methanone (10) and (2,6-dibromo-3,4,5-trimethoxyphenyl) (3,4-dimethoxyphenyl) methanone (11) were synthesized with the bromination of diarylmethanone 7 with ceric (IV) ammonium nitrate (CAN/LiBr). In order to determine the structures of the compounds synthesized, IR, HRMS, 1H and 13C NMR spectroscopic analysis were used. Geometrical parameters of the products were optimized with the density functional theory (DFT) B3LYP method using the 6-311G(d,p) basis set implemented Gaussian 09 and analyzed their structural parameters (bond lenghts, bond angles, dihedral angles).