Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.1/4232
Título: Photoisomerization of saccharin
Autor: Duarte, L.
Reva, I. D.
Cristiano, Maria Lurdes Santos
Fausto, R.
Data: 2013
Editora: American Chemical Society
Citação: Duarte, Luis; Reva, Igor; Cristiano, Maria de Lurdes Santos; Fausto, Rui. Photoisomerization of Saccharin, The Journal of Organic Chemistry, 78, 7, 3271-3275, 2013.
Resumo: Most known applications of saccharin and saccharyl derivatives and their potential for new uses rely on the thermal and photochemical stability of the saccharyl system. Here, we show that saccharin undergoes structural rearrangement when subjected to a narrow-band ultraviolet irradiation. Monomeric saccharin was isolated in low-temperature argon matrices and its photochemistry was characterized by means of infrared spectroscopy and DFT calculations. Among several DFT methods used, the O3LYP/6-311++G(3df,3pd) level gave the best match with the experimental spectra. Irradiation of matrix-isolated saccharin, with a narrow-band source (290 nm), generates a so far unknown isomer that we call iso-saccharin. The structures of the conjugate bases of saccharin and iso-saccharin were also computed theoretically. Their free energies and dipole moments suggest that both anions may be relevant in systems where saccharin participates, as is the case of the recently proposed saccharin-based ionic liquids.
Peer review: yes
URI: http://hdl.handle.net/10400.1/4232
DOI: http://dx.doi.org/10.1021/jo400191p|
ISSN: 0022-3263
Aparece nas colecções:CCM2-Artigos (em revistas ou actas indexadas)



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