Synthesis, Molecular Structure and Spectroscopic Studies of 6,6 ' -(1 E ,1 ' E )-(Ethane-1,2-Diylbis(azan-1-yl-1-ylidene
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TRUCTURE OF ORGANIC COMPOUNDS
Synthesis, Molecular Structure and Spectroscopic Studies of 6,6'-(1E,1'E)-(Ethane-1,2-Diylbis(azan-1-yl-1ylidene))bis(phenylmethan-1-yl-1-ylidene)bis(3-(Octyloxy)phenol) Hasan Tanaka,*, Seher Meralb, and Ayşen Alaman Ağarc a Department
of Physics, Faculty of Arts and Sciences, Amasya University, Amasya, 05100 Turkey b Boyabat Vocational School, Sinop University, Sinop, Turkey c Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, Turkey *e-mail:[email protected] Received May 6, 2019; revised December 17, 2019; accepted December 19, 2019
Abstract—6,6'-(1E,1'E)-(ethane-1,2-diylbis(azan-1-yl-1-ylidene))bis(phenylmethan-1-yl-1-ylidene)bis(3(octyloxy)phenol) has been synthesized and characterized by FTIR, 1H, 13C NMR and single-crystal X-ray determination. The compound crystallizes in monoclinic space group C2/c with Z = 4 in the unit cell. The asymmetric unit of the compound contains one half-organic molecule. The molecule is located about a twofold rotation axis which bisects the central C14-C14i bond. The dihedral angle between the phenyl rings is 68.46(11)°. In the crystal, intramolecular O–H⋅⋅⋅N hydrogen bonds generates a six-membered ring, producing an S(6) ring motif. The crystal packing is also stabilized by C–H⋅⋅⋅π interactions. DOI: 10.1134/S1063774520070251
INTRODUCTION Schiff bases and its derivatives are an important class of compounds which can be used in a variety of studies such as organic synthesis, catalysis, drug design, industry and the life sciences [1–3]. Schiff bases have received much attention because of their potential applications with some of these compounds
N
N
OH HO O
exhibiting various pharmacological activities such as anticancer, anti-HIV, antibacterial and antifungal properties [4–7]. On the industrial scale, they have a wide range of applications, such as in dyes and pigments [8]. Due to the biological and industrial significance of the Schiff bases, we have synthesised derivatives of Schiff base, 6,6'-(1E,1'E)-(ethane-1,2-diylbis(azan1-yl-1-ylidene))bis(phenylmethan-1-yl-1-ylidene)bis(3(octyloxy)phenol) (Fig. 1), for the first time. In this study, we present the structure of 6,6'-(1E,1'E)-(ethane-1,2-diylbis(azan-1-yl-1-ylidene))bis(phenylmethan1-yl-1-ylidene)bis(3-(octyloxy) phenol) was studied by using FTIR, 1H NMR, 13C NMR, and X-ray crystallographic techniques. EXPERIMENTAL
O
Synthesis
Fig. 1. Chemical diagram of 6,6'-(1E,1'E)-(ethane-1,2diylbis(azan-1-yl-1-ylidene))bis(phenylmethan-1-yl-1ylidene)bis(3-(octyloxy)phenol).
6,6'-(1E,1'E)-(Ethane-1,2-diylbis(azan-1-yl-1ylidene))bis(phenylmethan-1-yl-1-ylidene)bis(3(octyloxy)phenol) was prepared by refluxing a mixture of a solution containing 2-hydroxy-4-octyloxybenzophenone (10.4 mg, 0.07 mmol) in tetrahydrofurane (THF) (20 mL) and a solution containing 1,2-etylenediamine (18.0 mg, 0.07 mmol) in THF (20 mL). The reaction mixture was stirred for 5 h under reflux. The obtained cyrstal material was yellow and washed with ethanol, dried at room temperature (m.p
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