A solid state NMR and X-ray crystallographic investigation of dynamic disorder in solid tetrahydronaphthalene derivatives

Abstract

The solid state disorder of two tetrahydronaphthalene derivatives, N-methyl-N-methoxy-5,6,7,8-tetrahydro-1-naphthamide and 5,6,7,8-tetrahydro-1-naphthoic acid, was studied by solid state NMR and single crystal X-ray diffraction. The X-ray crystal structure of N-methyl-N-methoxy-5,6,7,8-tetrahydro-1-naphthamide was obtained at 123 K. It indicated the presence of two distinct molecular conformations. Solid state 13C CP/MAS NMR data using the dipolar dephasing technique revealed that the two conformations of the molecule are dynamically disordered, while solid state 2H NMR data, collected on a specifically deuterated analog, were used to determine the populations of each conformation as well as an apparent activation energy. Solid state NMR experiments were also used to show that 5,6,7,8-tetrahydro-1-naphthoic acid possesses the same type of dynamic disorder. Key words: deuterium NMR, solid state NMR, dynamic disorder. X-ray, tetrahydronaphthalene derivatives