Experimental and computational thermochemical study of 2- and 3-thiopheneacetic acid methyl esters.
Thiophene-based compounds have widespread use in modern drug design, biodiagnostics, electronic and optoelectronic devices, and conductive polymers. The present study reports an experimental and computational thermochemical study on the relative stabilities of 2- and 3-thiopheneacetic acid methyl esters. The enthalpies of combustion and vaporization were measured by a rotating-bomb combustion calorimeter, Calvet microcalorimetry, and correlation gas chromatography, and the gas-phase enthalpies of formation at T=298.15 K were determined. Standard ab initio molecular orbital calculations at the G3 level were performed, and a theoretical study of the molecular and electronic structure of the compounds studied was carried out. Calculated enthalpies of formation, using atomization and isodesmic reactions are in very good agreement with the experimental results.
Roux
María Victoria
MV
Instituto de Química Física "Rocasolano", CSIC, Serrano 119, 28006 Madrid, Spain.
Temprado
Manuel
M
Notario
Rafael
R
Chickos
James S
JS
Santos
Ana Filipa L O M
AF
da Silva
Manuel A V Ribeiro
MA
D000085:Acetates / Q000737:chemistry*; D019342:Acetic Acid / Q000737:chemistry* / Q000378:metabolism; D003198:Computer Simulation; D015195:Drug Design; D004355:Drug Stability; D015394:Molecular Structure; D013816:Thermodynamics; D013876:Thiophenes / Q000737:chemistry* / Q000378:metabolism
D000085:Acetates; D013876:Thiophenes; D019342:Acetic Acid