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1 2003

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Structure of Pyridine-2-azo-p-phenyltetramethylguanidine

Borowiak T., Dutkiewicz G., Binkowska I., Jarczewski A.

Polish Journal of Chemistry

2003

Vol. 77 / nr 11

1427-1435

Replacement of dimethylamino group in pyridine-2-azo-p-dimethylaniline (PADA) by a stronger electron - releasing tetramethylguanidil (TMG) group forms a new complexing agent, pyridine-2-azo-p-phenyltetramethylguanidine (PAPT). The substitution does not enhance the expected complexing ability of PAPT in comparison with that of PADA. For steric reasons the tetramethylguanidil substituent CN3 and phenyl ring are not coplanar, which makes the resonance between them limited. This manifests in small contribution of quinoid form in the canonical structure distribution. The additivity of angular parameters in the phenyl ring is preserved.