3-Aryloxypropiononitriles Intermediates Crystal and Molecular Structure of 2- and 4-(2-Bromoethoxy)diphenylmethanes

J. ELLENA; G. PUNTE; J. C. AUTINO; G. P. ROMANELLI; A. E. GOETA

CRYSTAL RESEARCH AND TECHNOLOGY

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 1998 vol. 33 p. 145 - 151

0232-1300

The crystal structure of 2- and 4-(2-bromoethoxy)diphenylmethanes (I and II respectively), intermediates in a novel synthesis of substituted 3-aryloxypropiononitriles, have been determined by single crystal X-ray diffraction at room temperature (r.t.) and at 150K. No significant changes in the crystal structure of I and II have been observed in going from r.t. to 150K. In both compounds the bromoethoxy group presents a gauche conformation and shows a short Br.O intramolecular interaction that allows to explain the very good reaction yields obtained in the novel synthesis. The three-dimensional structure of I is stabilized by two intermolecular hydrogen bonds and that of II by six. This difference in the crystal packing of I and II explains the variation in the m.p. The analysis of 1H and 13C NMR spectra suggests that the molecular conformations in solution are similar to those found in solid state.