Infrared Spectroscopic Study of the Formamide-Na-Montmorillonite Complex. Conversion of s-Triazine to Formamide

T. T. Nguyen
C.S.I.R.O. Division of Soils, Private Mail Bag No. 2, Glen Osmond South Australia 5064, Australia

Abstract: The adsorption and degradation on montmorillonite of s-triazine, the parent compound of a major group of triazine-based herbicides, were studied by Fourier-transform infrared spectroscopy. The original s-triazine appeared to hydrolyze with residual bound water in montmorillonite at 20°C to produce formamide, which formed an intercalate with the clay. A mechanism for the conversion of s-triazine to formamide was proposed which does not support earlier reports that formic acid and ammonia are the reaction products. The infrared spectrum of the formamide-Na-montmorillonite intercalate suggests that formamide reacted with the exchangeable Na cation and that the NH2 group hydrogen bonded with the clay. Assuming the intercalated formamide molecule to be planar, the molecular plane was found to be inclined at ∼33° with respect to the plane of the silicate sheet. C-N and C-O bonds were also found to be tilted at the same angle with respect to the clay surface. The proposed orientation is in good agreement with the measured value of d(001) for the formamide-Na-montmorillonite complex. The proposed model of the formamide-montmorillonite complex serves as a basis for comparison of other clay-amide complexes that are important in protein-clay interactions.

Key Words: Formamide • Herbicide • Hydrolysis • Infrared spectroscopy • Intercalation • Montmorillonite • s-Triazine

Clays and Clay Minerals; October 1986 v. 34; no. 5; p. 521-528; DOI: 10.1346/CCMN.1986.0340504
© 1986, The Clay Minerals Society
Clay Minerals Society (www.clays.org)