Abstract

New Azo compounds containing an 1,8-naphthalimide moiety were synthesized from 1, 8-naphthalic anhydride by a reaction with p-phenylenediamine or benzidine to produce 1,8-naphthalimide derivatives (1 or 2), which were converted to diazonium salt derivatives by using sodium nitrite and acetic acid at 0-5 áµ’C. The diazonium salt was subjected to a coupling reaction with different substituted phenol in alkaline media at 0-5 áµ’c to produce azo compound derivatives (3-14).
 The New Azo compound derivatives (3-14) were identified by 1H-NMR, 13C-NMR, and FTIR and by measuring characteristic physical properties and specific reactions. Also, the ability of the prepared azo compounds to work as acid-base indicator was investigated, since azo dyes have different and sharp colors in acidic or basic solutions.

Highlights

  • PH indicators or acid-base indicators are halo chromic weak acids or bases which change their structures upon the pH change in solution

  • Some of the azo compounds have two tautomeric forms such as methyl orange and methyl red, each one has a different color and can be transformed from one form to another depending on the pH level of the environment, they are used as pHindicator

  • This property is very useful to detect the pH-level and was used extensively by researchers in various fields; it is employed in biological research to determine the acidity of the living media [4] and in analytical chemistry to detect the end point in acid-base titration.[5]

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Summary

Introduction

PH indicators or acid-base indicators are halo chromic weak acids or bases which change their structures upon the pH change in solution. -‫نفثال أيمايد و دراسة قابليتها كدالئل حامض‬-1,8 ‫تحضير و تذخيص مركبات ازو جديدة مرتبطة بـ‬ 1H-NMR spectrum of compound 1 showed a singlet signal of (-NH2) protons at δ= 5.28 ppm and multi signals aromatic protons at δ= 6.95-8.56 ppm, as shown in Table-2 and Figure-1.

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