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Synthesis and Structure of N,N’-Butylene-N,N’-hexylenebis(2-oxy-1-naphthaldimine)

Tomislav Friščić ; Department of Chemistry, Laboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Ul. kralja Zvonimira 8, 10000 Zagreb, Croatia
Branko Kaitner ; Department of Chemistry, Laboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Ul. kralja Zvonimira 8, 10000 Zagreb, Croatia
Ernest Meštrović ; Department of Chemistry, Laboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Ul. kralja Zvonimira 8, 10000 Zagreb, Croatia

Sažetak

The title compounds were synthesized in the reaction of 2-hydroxy- 1-naphthaldehyde and corresponding aliphatic diamines. Standard TGA and DSC procedures were applied to characterize both compounds 1 and 2. The stereochemistry of the compounds in solid state was determined by the single crystal X-ray diffraction. Compound 1: C26H24N2O2, orthorhombic, space group Pbca, a = 8.142(2) Å, b = 9.097(3) Å, c = 28.812(8) Å, R = 0.032. Compound 2: C28H28N2O2, orthorhombic, space group Pbcn, a = 23.738(2) Å, b = 8.9933(8) Å, c = 10.4206(8) Å, R = 0.038. The molecules of both compounds 1 and 2 have an imposed centre of inversion in the middle of the aliphatic chain bridging two naphthaldimine moieties. The well known crystallographic D2h bond length pattern as well as quinoid effects were observed in the fused ring system in both cases. In both Schiff bases, the N−H⋅⋅⋅O type of intramolecular hydrogen bond was established. An additional intermolecular three-centre hydrogen bond links the molecules in 1.

Ključne riječi

Hrčak ID:

132327

URI

https://hrcak.srce.hr/132327

Datum izdavanja:

2.3.1998.

Posjeta: 609 *