[NHN]- HYDROGEN BRIDGES IN THE 1( AND [OHO])1 ADDUCT OF 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE WITH 3,4-FURANDICARBOXYLIC ACID/

1,8-Bis(dimethylamino)naphthalene (DMAN) hydrogen 3,4-furandicarboxyla te monohydrate crystallizes in the space group P2(1)/c, Z = 4, a = 11. 328 (3), b = 10.341(3), c = 19.915(5) angstrom, beta = 122.68(5)-degre es. The NHN+ hydrogen bond in protonated DMAN is relatively long (R(N) ...(N) = 2.621(3) angstrom), bent (less than with right parenthesis th rough it NHN = 155(2)-degrees) and asymmetric (r(N-H) = 1.06(2) angstr om). In deprotonated 3,4-furandicarboxylic acid (FDCA), the OHO- hydro gen bridge is also asymmetric (R(O...O) = 2.468(3) angstrom, less than with right parenthesis through it OHO = 167(3)-degrees, r(OH) = 1.04( 3) angstrom). These features are reflected in the infrared spectrum. T hus, the nu(NH) absorption band which is usually located at about 500 cm-1 is shifted markedly towards higher frequencies with the appearanc e of a broad band at about 2000 cm-1. The nu(OH) combination band at a bout 1000 cm-1 for the OHO- bridge is analogous to that determined for potassium hydrogen 3,4-furandicarboxylate by S. Jaulmes, Acta Crystal logr., Sect. B, 34 (1978) 116.