N,N-Dibutylanilinium hydrogen squarate

Abstract

ÁC 4 HO 4 À [systematic name: N,N-dibutylbenzenaminium 2-hydroxy-3,4-dioxocyclobut-1-en-1-olate], is composed of a protonated N,N-dibutylaniline cation with a hydrogen squarate monoanion (common names). The disparate bond lengths within the squarate anion suggest delocalization of the negative charge over only part of the squarate moiety. In the crystal, the squarate anions are linked by pairs of O-HÁ Á ÁO hydrogen bonds, forming inversion dimers with an R 2 2 (10) ring motif. The dimers are linked to the cations on either side by N-HÁ Á ÁO hydrogen bonds, and weak C-HÁ Á ÁO hydrogen bonds. These cation-anion-anion-cation units are linked by further C-HÁ Á ÁO hydrogen bonds, forming layers parallel to (102).

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“…The C = N bonds have a double bond character and are slightly longer than the expected value for a typical double C(sp2) = N(sp2) bond (1.279 Å) but shorter than those observed in the free ligands, in agreement with the NMR and IR analyses 16,34 . The bond lengths and angles in the cations ( 1 ) and ( 2 ) are within the reported ranges 8,35 . The nitrogen atom environment presents a tetrahedral distorted geometry.…”

“…16,34 The bond lengths and angles in the cations (1) and ( 2) are within the reported ranges. 8,35 The nitrogen atom environment presents a tetrahedral distorted geometry.…”