X-Ray and Fourier-transform infrared studies of 1,8-bis(dimethylaminomethyl)naphthalene. Comparison with 1,8-bis(dimethylamino)naphthalene

Abstract

The X-ray structure of a proton sponge, 1,8-bis(dimethylaminomethyl)naphthalene (DMAMN) has been determined and its FTIR spectrum investigated. The results are compared with previously reported data on 1,8-bis(dimethylamino)naphthalene (DMAN). The X-ray results show that in DMAMN, the naphthalene ring is almost planar in contrast with DMAN. The IR spectra of these two molecules are markedly different and the decrease in the intensity of some ring and CH vibrational modes in DMAMN is discussed as a function of the higher symmetry of the naphthalene skeleton of the molecule.