Revisiting the thermal decomposition of five ortho-substituted phenyl azides by calorimetric techniques

• Published in: Journal of thermal analysis and calorimetry Vol. 100; no. 1; pp. 191 - 198
• Main Authors: Cardillo, Paolo, Gigante, Lucia, Lunghi, Angelo, Zanirato, Paolo
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 01.04.2010; Springer
• Subjects: Analytical Chemistry; Calorimetry; Chemistry; Chemistry and Materials Science; Differential scanning calorimetry; Estimates; Exact sciences and technology; Inorganic Chemistry; Measurement Science and Instrumentation; Methods; Nitrobenzenes; Noncondensed benzenic compounds; Organic chemistry; Phenyls; Physical Chemistry; Polymer Sciences; Preparations and properties; Solid phases; Thermal analysis; Thermal decomposition; Thermodynamics; DSC; TGA-FTIR; Kinetic and thermodynamic parameters; C80 techniques; MS (EI) spectroscopy; Pericyclic reactions and mechanism; Thermal decomposition ion in ‘solution phase’ and ‘solid phase’; Heat flux calorimetry; Phenyl azides; Fourier transformation; Alcohol; Heat flow; Reaction mechanism; Differential scanning calorimetry; Pyrolysis; Organic azide; Thermogravimetry; Aldehyde; Ketone; Infrared spectrometry; Thermal decomposition ion in 'solution phase' and 'solid phase'; Benzenic compound; Pericyclic reaction; Thermal analysis; Kinetics; Thermodynamic properties; Mass spectrometry
• ISSN: 1388-6150; 1588-2926; 1572-8943
• DOI: 10.1007/s10973-009-0572-8

The thermal decomposition (TD) of 2-azidophenylmethanol ( 1 ), 2-azidobenzenecarbaldehyde ( 2 ), 1-(2-azidophenyl)-1-ethanone ( 3 ), (2-azidophenyl)(phenyl)methanone ( 4 ) and 1-azido-2-nitrobenzene ( 5 ) was analysed by DSC, TG and C80 calorimetric techniques under both oxidative and non-oxidative conditions. The TD of these azides in solution is well known to give the corresponding benzoxazoles, generally in good yields, with the exception of azide 1 . When both the outcomes from the solid phase and in ‘solution phase’ TD reactions combined with the results from EI-MS experiments were considered, sufficient information was available to estimate the azides intrinsic molecular reactivity (MIR).