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

Friščić, Tomislav and Kaitner, Branko and Meštrović, Ernest (1998) Synthesis and Structure of N,N'-Butylene-N,N’-hexylenebis(2-oxy-1-naphthaldimine). Croatica Chemica Acta, 71 (1). pp. 87-98. ISSN 0011-1643

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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.

Item Type: Article
Date: 1998
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Faculty of Science > Department of Chemistry
Publisher: Hrvatsko kemijsko društvo
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Depositing User: mag. bibl. Ana Šafran
Date Deposited: 28 May 2014 11:24
Last Modified: 28 May 2014 11:24

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