The X-ray structure of a proton sponge, 1,8-bis(dimethylaminomethyl)naphthalene (DMAM N) has been determined and its FTI R 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. * For details of the CCDC deposition scheme, see 'Instructions for Authors (1994),'

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The 'H and 13C NMR spectra of the complex between 1,8-bis(dimethylarnino)naphthalene and 3,5dichlorophenol have been studied at temperatures between 30 "C and -70 "C in CD,Cl, and at different acid to base concentration ratios. At a temperature of -60 "C a splitting of the 'H and 13C signals of DMAN and DMANH+ is observed. The protonation degree deduced from the NMR data and the intensity of the Bohlmann bands are in very good agreement. At a temperature below 8 "C, a splitting (2.6 Hz) of the methyl protons caused by spin-spin coupling with the (NHN)+ bridge protons is observed. Comparison with literature data and with the coupling constant determined in this work for protonated N,Ndimethylaniline suggest that the potential surface of the NHN+ cation includes two symmetrically situated wells between which fast proton migration takes place.

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