BOND DISTANCES AND BOND ANGLES OF THE C-10 SKELETON IN NAPHTHALENE DERIVATIVES AS HARD BOND PARAMETERS - CL-35 NQR AND STRUCTURE OF 1,8-DIAMINONAPHTHALENE CL2HCCOOH, 1,8-DIAMINONAPHTHALENE CL3CCOOH, 1-AMINONAPHTHALENE CL3CCOOH, AND 1,8-DIAMINONAPHTHALENE

The structures of sever-al naphthalene derivatives and their Cl-35 NQR spectra have been investigated. 1,8-Diaminonaphthalene, C2v9-Pna2(1), Z = 8, a (in pm) = 881, b = 1577, c = 1213; 1,8-diaminonaphthalene monodichloroacetate, C2h6-C2/c, Z = 8, a = 2050, b = 584, c = 2333, beta (in degrees) = 110. 1; 1,8-diaminonaphthalene monotrichloroacetate, C-1(1)-P1BAR, Z = 2, a = 1211, b = 1062, c = 589, alpha = 74.8, beta = 80.1, gamma = 70.9; 1-aminonaphthalene trichloroacetate, D2h15-Pbca, Z = 8, a = 2347, b = 1289, c = 889. The Cl-35 NQR spectrum of 1,8-diaminonaphthalene monodichloroacetate is a doublet, the frequencies decreasing with increasing temperature from 77 to 217 K at which temperature T(b) the NQR signals bleach out. A Cl-35 NQR triplet is found for 1,8-diaminonaphthalene monotrichloracetate in the range 77 less-than-or-equal-to T/K less-than-or-equal-to 207 (=T(b)). 1-Amino-naphthalene trichloroacetate shows a Cl-35 NQR triplet, too, with T(b) = 136 K. Characteristic for the intermolecular interactions are hydrogen bonds in the chloroacetic acid salts; each NH3 groUP forms three hydrogen bonds, and of the two oxygens one is involved in two such bonds, one in one bond. Thereby units of two cations and two anions are formed, and these dimers are connected to strings by hydrogen bonds. Additional van der Waals interactions between the chlorine atoms and the naphthalene ring system are observed. Comparison of the intramolecular bond distances C(i)-C(j) of the C10 naphthalene skeleton for 41 naphthalene derivatives (present data and literature) shows that the bond distances C(i)-C(j) are little influenced by substitution, as is the mean bond length. Shorter and longer distances prove a partial localization of charge at C(1)-C(2), C(3)-C(4), C(5)-C(6), and C(7)-C(8). Regularities within the bond angles and characteristic influences of 1,8-disubstitution on it are discussed.