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Journal of the Iranian Chemical Society

, Volume 13, Issue 5, pp 931–943 | Cite as

Solvatochromic responses and pH effects on the electronic spectra of some azo derivatives of 1-amino-2-hydroxy-4-naphthalenesulfonic acid

  • Mamdouh S. Masoud
  • Ahmed M. RamadanEmail author
  • Amina A. Soayed
  • Sherif M. S. Ammar
Original Paper

Abstract

Synthesis and characterization of five arylazo derivatives of 1-amino-2-hydroxy-4-naphthalenesulfonic acid (H2L1) are reported. The UV/Vis absorption spectra of the parent compound (H2L1) and its arylazo derivatives (H2L2–H4L6) have been measured at room temperature in seven solvents of different polarities and with variable parameters. The electronic transitions were analyzed using SPSS program, linear regression technique and Kamlet–Taft’s equation to permit a good understanding of solvent-induced spectral shifts. The electronic absorption spectra of the prepared compounds containing different substituents were studied in aqueous solutions at different pH values. The pK values of the investigated compounds were evaluated spectrophotometrically. The prevailing acid species present at any pH range are judged from the constructed distribution diagrams.

Keywords

Naphthalenesulfonic acid Diazotization Solvatochromism pH effect 

Supplementary material

13738_2016_809_MOESM1_ESM.bmp (2.2 mb)
Effect of solvents on the electronic absorption spectra of H2L1 (BMP 2284 kb)
13738_2016_809_MOESM2_ESM.bmp (643 kb)
Effect of pH on the electronic absorption spectra of 1 10-4 M of H2L1 (BMP 643 kb)
13738_2016_809_MOESM3_ESM.bmp (643 kb)
Effect of pH on the electronic absorption spectra of 1 10-4 M of H2L2 (BMP 643 kb)
13738_2016_809_MOESM4_ESM.bmp (643 kb)
Effect of pH on the electronic absorption spectra of 1 × 10-4 M of H3L3 (BMP 643 kb)
13738_2016_809_MOESM5_ESM.bmp (643 kb)
Effect of pH on the electronic absorption spectra of 1 × 10-4 M of H3L4 (BMP 643 kb)
13738_2016_809_MOESM6_ESM.bmp (643 kb)
Effect of pH on the electronic absorption spectra of 1 × 10-4 M of H3L5 (BMP 643 kb)
13738_2016_809_MOESM7_ESM.bmp (643 kb)
Effect of pH on the electronic absorption spectra of 1 × 10-4 M of H4L6 (BMP 643 kb)
13738_2016_809_MOESM8_ESM.doc (165 kb)
Supplementary material 8 (DOC 165 kb)

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Copyright information

© Iranian Chemical Society 2016

Authors and Affiliations

  • Mamdouh S. Masoud
    • 1
  • Ahmed M. Ramadan
    • 1
    • 2
    Email author
  • Amina A. Soayed
    • 1
    • 3
  • Sherif M. S. Ammar
    • 1
  1. 1.Faculty of Science, Chemistry DepartmentAlexandria UniversityAlexandriaEgypt
  2. 2.Faculty of Science, Chemistry DepartmentKing Khalid UniversityAbhaSaudi Arabia
  3. 3.Faculty of Medicine, Chemistry DepartmentDammam UniversityDammamSaudi Arabia

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