New N-aryloxy-phthalimide derivatives. Synthesis,physico-chemical properties,and QSPR studies |
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Authors: | Madalina Tudose Florin D. Badea Miron T. Caproiu Adrian Beteringhe Maria Maganu Petre Ionita Titus Constantinescu Alexandru T. Balaban |
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Affiliation: | (1) PG Department of Studies in Chemistry, Karnatak University, Dharwad, 580003, India; |
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Abstract: | Starting from N-hydroxyphthalimide 1 and the reactive fluoro- or chloro-nitroaryl derivatives 2, 3 and 4a-e (2-chloro-3,5-dinitropyridine; 3, NBD-chloride; 4a, 1-fluoro-2,4-dinitrobenzene; 4b, picryl chloride; 4c, 4-chloro-3,5-dinitrobenzotrifluoride; 4d, 2-chloro-3,5- dinitrobenzotrifluoride; 4e, 4-chloro-3,5-dinitrobenzoic acid) the corresponding N-(2-nitroaryloxy)-phthalimide derivatives 5a-e, or 6 and 7 were obtained and characterized by IR, UV-Vis 1H-NMR and 13C-NMR spectroscopy. The TLC behavior and the hydrophobicity of these derivatives have been experimentally evaluated by RM0 parameters (using RP-TLC). The experimental RM0 parameters were compared with the calculated partition coefficient, log P. A QSPR study was also performed to establish possible correlations between the structure and physical properties (λmax and RM0) of compounds 5a-e, 6, and 7. ![MediaObjects/11532_2010_63_Fig1_HTML.jpg](/content/2042806522505343/MediaObjects/11532_2010_63_Fig1_HTML.jpg) |
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