CRYSTAL AND MOLECULAR-STRUCTURE AND IR-SPECTRA OF THE 1/1 AND 1/2 ADDUCTS OF 1,8-BIS(DIMETHYLAMINOMETHYL)NAPHTHALENE WITH PICRIC ACID

The 1:1 and 1:2 adducts of 1,8-bis(dimethylaminomethyl)naphthalene (DMAMN) with picric acid were isolated. Both adducts crystallize in the space group P1BAR. The unit cell parameters for the 1:1 adduct are a = 9.461(3), b = 11.608(5), c = 11.872(5) angstrom, alpha = 70.32(3), beta = 71.32(3) and gamma = 81.22(3)-degrees, Z = 2, and those for the 1:2 adduct are a = 10.563(3), b = 11.035(4), c = 15.282(4) angstrom, alpha = 105.06(3), beta = 100.35(3) and gamma = 106.24(3)-degrees, Z = 2. The NHN+ intramolecular hydrogen bond in the 1:1 adduct is relatively long (2.716(3) angstrom), much longer than such bonds in protonated 1,8-bis(dimethylamino)naphthalene (DMAN) (2.55-2.65 angstrom) and DMAMN nitrate (2.642(3) angstrom). In doubly protonated DMAMN two non-equivalent N+H...O-bridges are formed. The crystallographic data are in good agreement with the IR spectroscopic behaviour.