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https://hdl.handle.net/10316/10487
Título: | Thermally Induced Sigmatropic Isomerization of Pseudosaccharyl Allylic Ether | Autor: | Gómez-Zavaglia, A. Kaczor, A. Almeida, R. Cristiano, M. L. S. Eusébio, M. E. S. Maria, T. M. R. Mobili, P. Fausto, R. |
Data: | 16-Abr-2009 | Editora: | American Chemical Society | Citação: | The Journal of Physical Chemistry A. 113:15 (2009) 3517-3522 | Resumo: | The thermally induced sigmatropic isomerization of the pseudosaccharyl allylic ether [3-(allyloxy)-1,2-benzisothiazole 1,1-dioxide; ABID] has been investigated by a multidisciplinary approach using temperature dependent infrared spectroscopy, differential scanning calorimetry, and polarized light thermomicroscopy, complemented by theoretical methods. Migration of the allylic system from O to N occurs in the melted ABID, and the thermally obtained 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) starts to be produced at ca. 150 °C, in a process with an activation energy of 92 kJ mol−1. From kinetic data, a concerted [3,3′] sigmatropic mechanism is proposed. In the temperature range investigated, ABIOD was found to exhibit polymorphism. Cooling of the molten compound leads to the production of a metastable crystalline form, which upon annealing at room temperature might be transformed to the stable crystalline phase. ABID shows a single crystalline variety. Assignments were proposed for the infrared spectra of the observed neat condensed phases of the two compounds. | URI: | https://hdl.handle.net/10316/10487 | ISSN: | 1089-5639 | DOI: | 10.1021/jp8112254 | Direitos: | openAccess |
Aparece nas coleções: | FCTUC Química - Artigos em Revistas Internacionais |
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Thermally Induced Sigmatropic Isomerization of Pseudosaccharyl.pdf | 566.86 kB | Adobe PDF | Ver/Abrir |
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