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Chem.Abstr. 1968 , vol. 68, # 95185

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Electronic properties of N-heteroaromatics. XIV. Charge-transfer interactions between 4-nitropyridine 1-oxide and aniline derivatives

By Okano, Teisuke; Uekama, Kaneto; Isawa, Yutaka; Tsukuda, Kazuhisa
From Yakugaku Zasshi (1967), 87(11), 1309-14. | Language: Japanese, Database: CAPLUS

Spectrophotometric studies were made on the interactions between 4-nitropyridine 1-oxide (I) and aniline derivs., and participation of n-π* type charge-transfer in the complex formation, wherein the amine moiety of PhNH2 acts as the electron donor and I as electron acceptor, was deduced from the following results. (1) New absorption bands which appeared in the visible region of the differential spectra of mixed solns. of I and aniline derivs. were characteristic of charge-transfer complexes in that they shifted toward red with increasing polarity of the solvents. (2) From the gradient of the straight line obtained by plotting Z-values of solvents versus transition energies of the complexes of I and aniline derivs. in various solvents, it was clarified that the new absorption bands were assignable to n → π* transitions. (3) The new absorption bands were susceptible to pH changes and diminished in the acid range, indicating participation of an n electron of the amino group of the aniline in the complex formation. (4) Examn. of ε, K, and ΔH values of complexes of I and the aniline revealed that methylation of the NH2 group of the aniline had a steric hindrance effect on complex formation.

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