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

• Authors: Madalina Tudose , Florin Badea , Miron Caproiu , Adrian Beteringhe , Maria Maganu , Petre Ionita , Titus Constantinescu , Alexandru Balaban
• Languages of publication: EN

Abstracts

EN

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. [...]

Keywords

EN

N-aryloxy-phthalimide derivatives; UV-Vis; TLC; RP-TLC; QSPR

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 4
• Pages: 789-796

Dates

published

1 - 8 - 2010

online

17 - 6 - 2010

Contributors

author

Madalina Tudose

• Institute of Physical Chemistry, 202 Splaiul Independentei, Bucharest, 060021, Romania

author

Florin Badea

• Organic Chemistry Department, University Politehnica Bucharest, Bucharest, 011061, Romania

author

Miron Caproiu

• Center of Organic Chemistry, 202 Splaiul Independentei, Bucharest, 060023, Romania

author

Adrian Beteringhe

• Institute of Physical Chemistry, 202 Splaiul Independentei, Bucharest, 060021, Romania

author

Maria Maganu

• Center of Organic Chemistry, 202 Splaiul Independentei, Bucharest, 060023, Romania

author

Petre Ionita

author

Titus Constantinescu

• Institute of Physical Chemistry, 202 Splaiul Independentei, Bucharest, 060021, Romania

author

Alexandru Balaban

• Texas A&M University at Galveston, Galveston, TX, 77551, USA

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Identifiers

DOI

10.2478/s11532-010-0063-6