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Synthesis, structural and spectroscopic properties of a new Schiff base ligand N,N′-bis(trifluoromethylbenzylidene)ethylenediamine

Lookup NU author(s): Professor Mohammad Habibi, Dr Ross Harrington, Emeritus Professor Bill Clegg

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Abstract

The Schiff base compound, N,N′-bis(trifluoromethylbenzylidene)ethylenediamine (C18H14F6N2) (1), CF3C6H4CHNCH2CH2NCHC6H4CF3 has been synthesized by adding a solution of ethylenediammine (en), 0.1 mmol in chloroform to 4-(trifluoromethyl)-benzaldehyde, CF3C6H4CHO (0.2 mmol) and the product was crystallized in ethanol with the mp, 109.2 °C and 75% yield. The crystal structure was investigated by a single-crystal X-ray diffraction study at 150 K. The compound crystallizes in monoclinic space group, P21/c with a = 9.295(3), b = 5.976(5), c = 15.204(9) Å and α = 90°, β = 96.56(5)° and γ = 90°. The crystal structure is stabilized by intermolecular C{single bond}H · · · F hydrogen bonds. The asymmetric unit contains only one-half of the molecule related to the center of symmetry coinciding with C(1)-C(1′) and as a whole, the title molecule is in the staggered conformation. The phenyl rings and the C{double bond, long}N imine bonds are co-planar. The infrared spectrum showed a sharp peak at 1640 cm-1 which is typical of the conjugated C{double bond, long}N stretching and strong peaks at 800-1400 cm-1 regions are due to the C-C and C-H stretching modes. Electronic absorption spectra exhibits strong absorption in the UV region (240 nm wavelength) which have been ascribed to π - π1*, π - π2* and π - π3* electronic transitions. The 1H NMR spectra showed three distinct peaks at 2.5, 7.8 and 8.5 ppm which are assigned based on the splitting of resonance signals and are clearly confirmed by the X-ray molecular structure. The aromatic protons appear at about 7.8 ppm and the imine protons at 8.5 ppm. The sharp singlet at about 3.95 ppm is assigned to the CH2-CH2 protons. Mass spectra of the titled compound showed the molecular ion peak at m/e 372 (M+), and fragments at m/e 353 (M-F), 342 (M-2F), 200 (M-CF3C6H4CHN), 186 (M-CF3C6H4CHNCH2). © 2006 Elsevier B.V. All rights reserved.


Publication metadata

Author(s): Habibi MH, Montazerozohori M, Lalegani A, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: Journal of Fluorine Chemistry

Year: 2006

Volume: 127

Issue: 6

Pages: 769-773

ISSN (print): 0022-1139

ISSN (electronic): 1873-3328

Publisher: Elsevier SA

URL: http://dx.doi.org/10.1016/j.jfluchem.2006.02.014

DOI: 10.1016/j.jfluchem.2006.02.014


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