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

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,* , 2
,
3
 and
2
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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