Energetic study of bromobenzonitrile isomers: insights on the intermolecular interactions, aromaticity and electronegativity

• Type: Article in International Scientific Journal
• Date: 2013

Authors

Ines M Rocha (Author) Other; Tiago L P Galvao (Author) Other; Maria D M C R Ribeiro da Silva (Author) FCUP; Manuel A V R Ribeiro da Silva (Author) Other

Journal

Title: Structural Chemistry

Vol. 24

Pages: 1935-1944

ISSN: 1040-0400

Publisher: Springer Nature

Indexing

ISI Web of Knowledge - 10 Citations

Scopus - 10 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-006-JBA

DOI: 10.1007/s11224-013-0278-1

Abstract (EN): The standard (p degrees = 0.1 MPa) molar enthalpies of formation, in the gaseous phase, of 2-, 3- and 4-bromobenzonitrile isomers were calculated from the combination of the following two parameters experimentally determined: the standard molar enthalpy of formation in the condensed phase, derived from the standard molar energy of combustion in oxygen at T = 298.15 K, measured by rotating-bomb combustion calorimetry, and the standard molar enthalpy of sublimation at the same reference temperature, derived from vapour pressure studies at several temperatures, as measured by mass-loss Knudsen effusion. The computational calculations complement the energetic study and analysis of the electron delocalization allows a comparison between the fluorine and bromine benzonitrile isomers. The harmonic oscillator model of aromaticity and nucleus-independent chemical shift aromaticity criteria and the natural bond orbital analysis were applied and related with the intramolecular enthalpic interactions. The intermolecular interactions in the crystal packing were analysed in terms of enthalpic and entropic contributions, using the crystallographic structures available in literature.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10