Theoretical considerations regarding the thione-thiol tautomerism in 2-(5-mercapto-1,3,4-thiadiazol-2-ylthio)acetic acid

Authors

  • Raluca Oana Pop University of Medicine and Pharmacy "Victor Babes" Timisoara, Faculty of Pharmacy
  • Maria Ilici University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICAM Department
  • Mihaiela Andoni University of Medicine and Pharmacy “Victor Babeş” Timisoara, Faculty of Pharmacy, Eftimie Murgu Square 2, 300041 Timişoara, Romania
  • Vasile Nicolae Bercean University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICON Department
  • Cornelia Muntean University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICAM Department
  • Monica M. Venter Babeş-Bolyai” University, Faculty of Chemistry and Chemical Engineering, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania
  • Ilie Julean University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICAM Department

DOI:

https://doi.org/10.17344/acsi.2014.567

Keywords:

thiadiazole, pKa, thiol-thione tautomerism, theoretical computations, DFT

Abstract

The acidity constants Ka1 and Ka2 of 2-(5-mercapto-1,3,4-thiadiazol-2-ylthio)acetic acid have been determined both by experimental and theoretical methods. pKa computations at B3LYP/6-311+G(d,p) level of theory were carried out for the two tautomeric forms, thiol and thione, of the above-mentioned acid. Comparisons between the experimental and theoretical values led to the establishing of the most stable tautomer of 2-(5-mercapto-1,3,4-thiadiazol-2-ylthio)acetic acid in aqueous solution. Also, a DFT study regarding the reactivity, aromaticity and population analysis of the two tautomers has been performed.

Author Biographies

Raluca Oana Pop, University of Medicine and Pharmacy "Victor Babes" Timisoara, Faculty of Pharmacy

Faculty of Pharmacy, Department I

Lecturer

Maria Ilici, University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICAM Department

PhD student

Mihaiela Andoni, University of Medicine and Pharmacy “Victor Babeş” Timisoara, Faculty of Pharmacy, Eftimie Murgu Square 2, 300041 Timişoara, Romania

Lecturer

Vasile Nicolae Bercean, University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICON Department

Lecturer

Cornelia Muntean, University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICAM Department

Lecturer

Monica M. Venter, Babeş-Bolyai” University, Faculty of Chemistry and Chemical Engineering, 11 Arany Janos Str., 400028 Cluj-Napoca, Romania

Associate Professor

Ilie Julean, University POLITEHNICA Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, 300006 Timisoara, Romania CAICAM Department

Professor

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Published

06.02.2015

Issue

Vol. 62 No. 1 (2015)

Section

Physical chemistry

License

Except where otherwise noted, articles in this journal are published under the Creative Commons Attribution 4.0 International License