2,1,3-Benzothiadiazole: Study of its structure, energetics and aromaticity

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Margarida S Miranda (Author) FCUP; Agostinha A R Matos (Author) FCUP; Victor M F Morais (Author) ICBAS; Joel F Liebman (Author) Other

Journal

Title: Journal of Chemical Thermodynamics

Vol. 50

Pages: 30-36

ISSN: 0021-9614

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 7 Citations

Scopus - 7 Citations

Scientific classification

FOS: Engineering and technology > Mechanical engineering

Other information

Authenticus ID: P-002-8TH

DOI: 10.1016/j.jct.2012.02.005

Abstract (EN): The present work reports an experimental study on the energetics of 2,1,3-benzothiadiazole and a computational study on its structure, energetics and aromaticity. In the experimental part the standard (p(o) = 0.1 MPa) massic energy of combustion, at T = 298.15 K, was measured by rotating bomb combustion calorimetry, in oxygen, and allowed the calculation of the respective standard molar enthalpy of formation, in the crystalline phase, at T = 298.15 K. The standard molar enthalpy of sublimation, at T = 298.15 K, was measured by high-temperature Calvet microcalorimetry. From the combination of data obtained by both techniques we were able to calculate the respective standard molar enthalpy of formation, in the gas phase, at T = 298.15 K: (276.6 +/- 2.5) kJ . mol (1). This thermochemical parameter was compared with estimates obtained from high level ab initio quantum chemical calculations using the G3(MP2)//B3LYP composite method and various appropriately chosen reactions. The molecular structure of 2,1,3-benzothiadiazole was obtained from DFT calculations with the B3LYP density functional and various basis sets: 6-31G(d), 6-311(d, p), 6-311+G(3df, 2p), aug-ccpVTZ and aug-ccpVQZ and its aromaticity and that of some related molecules were evaluated by analysis of nucleus independent chemical shifts (NICS) values.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7