Effect of β-cyclodextrin on the hydrolisis of N-phenylphtalamide and N-adamantylphtalamide - A two-sided semiempirical approach

ALEJANDRO M. GRANADOS; R. HOYOS DE ROSSI; D.A. BARBIRIC; E.A. CASTRO

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Año: 2002 vol. 619 p. 91 - 100

0166-1280

Complexes of β-cyclodextrin including N-phenylphtalamide, N-adamantylphtalamide or their respective intermediates occurring during intramolecular amide hydrolysis were calculated by means of the PM3 and molecular mechanics programs. Structural features of the complexes, energy changes and mutual interactions are comparatively analyzed in order to explain the behavior differences that were experimentally observed between the two-substrate families. Some convergence characteristics are also commented.