New N-aryloxy-phthalimide derivatives. Synthesis, physico-chemical properties, and QSPR studies

Central European Journal of Chemistry - Tập 8 - Trang 789-796 - 2010
Madalina Tudose1, Florin D. Badea2, Miron T. Caproiu3, Adrian Beteringhe1, Maria Maganu3, Petre Ionita1,4, Titus Constantinescu1, Alexandru T. Balaban5
1Institute of Physical Chemistry, Bucharest, Romania
2Organic Chemistry Department, University Politehnica Bucharest, Bucharest, Romania
3Center of Organic Chemistry, Bucharest, Romania
4Organic Chemistry Department, University of Bucharest, Bucharest, Romania
5Texas A&M University at Galveston, Galveston, USA

Tóm tắt

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.

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