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

• Autorzy: Olejnik Z. , Lis T. , Grech E. , Nowicka-Scheibe J.
• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

crystal structure; proton transfer; hydrogen bond; molecular structure

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 1998
• Tom: Vol. 72, nr 7
• Strony: 1255--1268
• Opis fizyczny: Bibliogr. 18 poz., tab.

Twórcy

autor

Olejnik Z.

autor

Lis T.

autor

Grech E.

autor

Nowicka-Scheibe J.

• Faculty of Chemistry University of Wrocław F. Joliot-Curie 14 50-383 Wrocław Poland,