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Molecules 2011, 16(10), 8788-8802; doi:10.3390/molecules16108788

Synthesis, Acidity Constants and Tautomeric Structure of the Diazonium Coupling Products of 2-(Benzylsulfanyl)-7H-purin-6-one in Its Ground and Excited States

1
Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt
2
Department of Chemistry, Faculty of Science, University of Taif, Taif, 888, Saudi Arabia
3
National Institute of Laser-enhanced Sciences, University of Cairo, Giza, 12613, Egypt
*
Author to whom correspondence should be addressed.
Received: 22 September 2011 / Revised: 7 October 2011 / Accepted: 12 October 2011 / Published: 19 October 2011
(This article belongs to the Special Issue Heterocycles)
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Abstract

A series of new 8-arylhydrazono-2-(benzylsulfanyl)-7H-purin-6-ones 6 were synthesized, their electronic absorption spectra in different organic solvents of varying polarities were investigated and their acid dissociation constants in both the ground and excited states were determined spectrophotometrically. The tautomeric structures of such products were elucidated by spectral analyses and correlation of their acid dissociation constants with the Hammett equation. The results indicated that the studied compounds 6 exist predominantly in the hydrazone tautomeric form 6A in both the ground and excited states.
Keywords: purine; diazonium coupling; azo compounds; tautomerism; ground; excited states purine; diazonium coupling; azo compounds; tautomerism; ground; excited states
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Darwish, E.S.; Mosselhi, M.A.; Altalbawy, F.M.; Saad, H.A. Synthesis, Acidity Constants and Tautomeric Structure of the Diazonium Coupling Products of 2-(Benzylsulfanyl)-7H-purin-6-one in Its Ground and Excited States. Molecules 2011, 16, 8788-8802.

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