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.
Highlights
Polymers of thiophenes have intense interest in literature due to their electrical properties and durability [1]
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
There is a linear correlation between the solvent-induced carbonyl frequency and energy values (R2=0.99951, 0.99906 and 0.99805 for 5F-2TC, 5C-2TC and 5B-2TC, respectively)
Summary
Polymers of thiophenes have intense interest in literature due to their electrical properties and durability [1]. For T2C, the cis form is defined as having the heaviest (generally nonhydrogen) atom of a substituent group cis to the ring sulfur atom. Rates of chemical reactions can vary many orders of magnitude depending on the solvent. In this sense, nature and effect of the solute-solvent interaction on the vibrational spectrum are well known [9]-[13]. There are numerous examples of the solvent effect on some group frequencies. The empirical approaches such as the Kirkwood-Bauer-Magat (KBM) [16],[17], solvent acceptor number (AN) [18], Swain [19] and linear solvation energy relationships (LSER) [20] have characterized the solvent effect on vibrational frequency
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