دورية أكاديمية
Experimental and theoretical studies of the photophysics of 7-amino-3-phenyl-2H-benzo[b] [1,4]oxazin-2-one in homogeneous solvents and b-cyclodextrin aqueous solutions
| العنوان: | Experimental and theoretical studies of the photophysics of 7-amino-3-phenyl-2H-benzo[b] [1,4]oxazin-2-one in homogeneous solvents and b-cyclodextrin aqueous solutions |
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| المؤلفون: | Valdebenito, Silvana, Zapata-Torres, Gerald, Lemp, Else, Zanocco, Antonio L. |
| المصدر: | Afinidad. Revista de química teórica y aplicada; Vol. 72, Núm. 569 (2015) Afinidad; Vol. 72, Núm. 569 (2015) |
| حالة النشر: | published |
| بيانات النشر: | Universitat Ramon Llull, 2015. |
| سنة النشر: | 2015 |
| مصطلحات موضوعية: | Aryloxazinones, solvent effect, fluorescent probes, b-cyclodextrin, inclusion complex, binding constants. |
| الوصف: | The photophysical behavior of 7-amino-3-phenyl-2Hbenzo[b][1,4]oxazin-2-one was studied in organic solvents and in aqueous solutions of b-cyclodextrin using steady-state fluorescence and computational chemistry methods. In homogeneous media, fluorescence spectra show a noteworthy solvatochromic effect leading to large Stokes shifts. Linear solvation energy relationship and Lippert-Mataga equation analysis of the Stokes shifts indicate an increase of the dipolar moment in the singlet excited state and the participation of a partial chargetransfer state in the deactivation process. Incorporation of 7-amino-3-phenyl-2H-benzo[b][1,4]oxazin-2-one into the b-cyclodextrin inner cavity was monitored by observing the increase of fluorescence as a function of the cyclodextrin concentration. Analysis of fluorescence data in terms of Job plots and the Benesi-Hildebrand equation are indicate the formation of a 1:1 complex. The binding constantobtained from Benesi-Hildebrand plots was 597 M-1 at 298K. Also, the values of thermodynamics parameters determinedfrom the dependence of the binding constant on thetemperature show that inclusion is an enthalpy-driven process.Docking studies suggest that the complex stability is due to favorable van der Waals interactions within the cavity and a hydrogen bond interaction between the amino substituent and hydroxyl groups located in the narrow rim of the cavity. The same conclusion was achieved employing the Molecular Mechanics Poisson-Boltzmann Surface Area methodology to determine the energy contributions to the total free energy for the inclusion process. |
| نوع الوثيقة: | article |
| وصف الملف: | application/pdf |
| اللغة: | English |
| تدمد: | 2339-9686 0001-9704 |
| العلاقة: | https://www.raco.cat/index.php/afinidad/article/view/291725/380224Test |
| الوصول الحر: | https://www.raco.cat/index.php/afinidad/article/view/291725Test |
| رقم الانضمام: | edsrac.291725 |
| قاعدة البيانات: | RACO (Revistes Catalanes amb Accés Obert) |
| تدمد: | 23399686 00019704 |
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