Carbonyl stretching vibrations of 5-halogen-2-thiophenecarboxaldehydes: KBM, AN, SWAIN and LSER parameters

Abstract

Halogen and solvent influence on the conformational stability and carbonyl stretching vibration of 5-Halogeno-2-thiophenecarboxaldehydes (C5H3XOS; X=F, Cl or Br) were investigated by the density functional theory using the B3LYP functional, 6-311+G(3df,p) basis set and polarizable continuum model. Calculations were performed by the cis and trans forms of the compounds in eighteen different solvents. The carbonyl stretching frequencies were correlated with some solvent parameters such as the Kirkwood-Bauer-Magat equation, the solvent acceptor number, Swain parameters and the linear solvation energy relationships. The findings of this research will be useful for thiophenecarboxaldehydes.

Keywords

• 5-Halogeno-2-thiophenecarboxaldehyde
• DFT
• Solvent effect

5-halojen-2-tiyofenkarboksaldehitlerin karbonil gerilme titreşimleri: KBM, AN, SWAIN ve LSER parametreleri

Öz

5-halojen-2-tiyofenkarboksaldehitlerin (C5H3XOS; X=F, Cl veya Br) yapısal denge ve karbonil gerilme titreşimleri üzerindeki çözücü ve halojen etkileri yoğunluk fonksiyoneli teorisi ile B3LYP fonksiyoneli, 6-311+G(3df,p) baz seti ve kutuplanabilir süreklilik modeli kullanılarak incelendi. Hesaplamalar on sekiz farklı çözücü içinde moleküllerin cis ve trans konformasyonları ele alınarak yürütüldü. Çözücü içindeki karbonil gerilme titreşim frekansları Kirkwood-Bauer-Magat denklemi, çözücü akseptör sayısı, Swain parametreleri ve lineer çözünme enerji ilişkisi gibi çözücü skalaları ile incelendi. Bu çalışmanın sonuçları tiyofen-karboksaldehit türevleri için faydalı olacaktır.

Anahtar Kelimeler

• 5-Halojen-2-tiyofenkarboksaldehit
• YFT
• Çözücü etkisi

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