Step-stool conformation of a cyclic Schiff base derived from ethylenediamine and heptane-2,4,6-trione: evidence for partial hydrolysis in metal coordination

Ranaweera, Samantha A.; Bruno, Donnadieu; Henry, W. P.; White, Mark. G.

doi:10.1107/s2053229622004582

Step-stool conformation of a cyclic Schiff base derived from ethylenediamine and heptane-2,4,6-trione: evidence for partial hydrolysis in metal coordination

Journal Article · 16 May 2022 · Acta Crystallographica. Section C, Structural Chemistry (Online)

DOI:https://doi.org/10.1107/s2053229622004582· OSTI ID:1980385

Ranaweera, Samantha A. ^[1]; Bruno, Donnadieu ^[2]; Henry, W. P. ^[2]; White, Mark. G. ^[2]

University of Ruhuna, Matara (Sri Lanka)
Mississippi State University, Starkville, MS (United States)

A Schiff base derived from ethylenediamine and heptane-2,4,6-trione, namely, 5,9,14,18-tetramethyl-1,4,10,13-tetraazacyclooctadeca-5,8,14,17-tetraene-7,16- dione (C₁₈H₂₈N₄O₂), abbreviated H₄daaden, was prepared and characterized for the first time by single-crystal X-ray diffraction. The atoms of the Schiff base occupy two different planes and thus the molecule is essentially nonplanar. An axis running through the C–C atoms of the ethylenediamine groups separate the two planes and these two planes are connected by bridging ethylene groups showing an angle of 117.34 (8)°. As a result, the side view of the molecule shows a ‘step-stool’ conformation. The nonplanar nature of the Schiff base plays an important role in metal coordination, which leads to partial hydrolysis of the ring structure

Research Organization:: Mississippi State Univ., Starkville, MS (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

DOE Contract Number:: FG36-06GO86025

OSTI ID:: 1980385

Journal Information:: Acta Crystallographica. Section C, Structural Chemistry (Online), Vol. 78, Issue 6; ISSN 2053-2296

Publisher:: International Union of Crystallography

Country of Publication:: United States

Language:: English

References (13)

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heptane-2
4
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ethylenediamine
cyclic Schiff base
crystal structure
stepstool conformation

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