Original scientific paper

Infrared Spectra of Aminophosphonic Acids. II.

V. Jagodić ; Institute »Ruder Boskovic«, 41000 Zagreb, Croatia, Yugoslavia
Lj. Tušek ; Institute »Ruder Boskovic«, 41000 Zagreb, Croatia, Yugoslavia

Abstract

Infrared spectra of diesters, monoesters and sodium salts of the
monoesters of several new aminophosphonic acids containing benzeneazo
group, e.g. derivatives of [a-(4-benzeneazoanilino)-N-benzyl]
phosphonic acid, and [4-benzeneazo-a-(anilino)-benzyl]phosphonic
acid, have been studied. Assignments for vibrations of the N-H,
P=O, Po2-, P-0-H and P-0-R (R =Et, Bu) groups in these
compounds were made. On the basis of the infrared spectra and
determination of molecular weights of the monoesters, the molecular
structure of the compounds is proposed. It was found that
the site of the benzeneazo group in the molecule influences the
properties of the monoesters. Thus, monoesters of [a-(4-benzeneazoanilino)-
N-benzyl]phosphonic acid are dimers in chloroform
solution, and are also associated, presumably dimeric, in the solid
state, owing to strong hydrogen bonds between phosphoryl and
acidic hydroxyl groups. Monoesters of [4-benzeneazo-a-(anilino)
benzyl]phosphonic acid exist in the solid state as zwitterions.

Keywords

Hrčak ID:

197193

URI

https://hrcak.srce.hr/197193

Publication date:

20.3.1973.

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