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1 Polish Journal of Chemistry

1 1998

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Comparison of the molecular structures of 1,5-bis(p-toluenesulphonamido)-2,4,6,8-tetranitronaphthalene and its dianion in the bispyridinium salt

100%

Olejnik Z. , Lis T. , Grech E. , Nowicka-Scheibe J.

tom Vol. 72, nr 7

1255-1268

1,5-Bis(p-toluenesulphonamido)-2,4,6.8-tetranitronaphthalene (1,5-TSATNN) [alternative name: N,N'-(2,4,6,8-tetranitronaphthalene-1,5-diyl)-bis(p-toluenesulphonamide)] crystalized from acetic acid or pyridine with three molar equivalents of solvent. The compound with pyridine is shown to be a 1:1 adduct of bispyridinium salt. Substantial differences between molecular geometries of 1,5-TSATNN and its dianion are found. Naphthalene cores are distorted from planarity in quite different modes and the neutral and deprotonated p-tosylamide groups adopt different rotational conformations. A significant delocalization of the negative charge, observed as shortening of the S-N and N(amide)-C bonds, as well as evidence of conjugation between the amide and nitro groups are found in the dianion.