(S)-(+)-1-(1-Naphthyl)-1-(2-thienylmethylene)ethylamine

Journal of Coordination Chemistry, 2020

Binuclear Ni(II) chelating complex with chiral Schiff base 1-((E)-(((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)imino)methyl)naphthalene-2-ol [Ni 2 L 2 ] has been synthesized. The structure of [Ni 2 L 2 ] was elucidated with single-crystal X-ray diffraction, spectroscopic (UV-vis, FTIR, mass) analysis and substantiated with computational (DFT) method. The crystal system of binuclear complex is monoclinic with space group P21/c. The asymmetric unit having two tridentate OON-donor sets are in slightly distorted square-planar geometry around each Ni(II) center. The distortion is due to strong coordination between two Ni(II) ions. The stabilization of complex [Ni 2 L 2 ] occurs due to noncovalent interactions and hydrogen bonding (C-H … C and C-H … O), H … H, O … H, C … H, and C-H … p stacking interactions, and van der Waals interactions. DFT optimization, with little acceptable discrepancies, correlate with the X-ray diffraction data as well as TD DFT optimization for electronic transitions of the complex showing acceptable alignment with spectroscopic data. The complex displays appreciable inclination towards DNA-binding with calf-thymus DNA (CT DNA) and the DNA-binding studies were carried out by UV-visible spectroscopy, fluorescence spectroscopy, cyclic voltammetry, viscosity measurements, and CD spectroscopy. The DNA-binding study reveals that the order of binding constant value is in 10 5 M 21 , supporting the effective efficiency of binding and the modes of binding are intercalation and groove.

Acta Crystallographica Section E Crystallographic Communications, 2016

Using a general solvent-free procedure for the synthesis of chiral Schiff bases, the following compounds were synthesized and their crystal structures determined: (S)-(+)-2-{[(1-phenylethyl)imino]methyl}naphthalene, C19H17N, (1), (S)-(+)-2-({[(4-methylphenyl)ethyl]imino}methyl)naphthalene, C20H19N, (2), (R)-(−)-2-({[(4-methoxylphenyl)ethyl]imino}methyl)naphthalene, C20H19NO, (3), (R)-(−)-2-({[(4-fluorophenyl)ethyl]imino}methyl)naphthalene, C19H16FN, (4), (S)-(+)-2-({[(4-chlorophenyl)ethyl]imino}methyl)naphthalene, C19H16ClN, (5), (S)-(+)-2-({[(4-bromophenyl)ethyl]imino}methyl)naphthalene, C19H16BrN, (6), (S)-(+)-2-({[1-(naphthalen-1-yl)ethyl]imino}methyl)naphthalene, C23H19N, (7), (S)-(+)-2-{[(1-cyclohexylethyl)imino]methyl}naphthalene, C19H23N, (8), (S)-(−)-2-{[(1,2,3,4-tetrahydronaphthalen-1-yl)imino]methyl}naphthalene, C21H19N, (9), and (+)-2-({[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]imino}methyl}naphthalene, C21H25N, (10). The moiety provided by the amine generates...

Proceedings of The 12th International Electronic Conference on Synthetic Organic Chemistry, 2008

The hexadentate Schiff base ligands were prepared by condensation of 3-ethoxy-2hydroxybenzaldehyde and different diamines (1,3-diaminopropane, 1,3-diamino-2,2-dimethylpropane, 1,4-diaminobutane) to yield H 2 L n (H 2 L 1 , H 2 L 2 and H 2 L 3 , respectively). The ligands have been characterised by elemental analysis, IR, 1 H and 13 C NMR spectroscopies and mass spectrometry (ES). The crystal structure of the H 2 L 2 ligand was solved by X-ray crystallography, revealing its ability to bind metal centres.

Proceedings of The 14th International Electronic Conference on Synthetic Organic Chemistry, 2010

The condensation of 3-methoxy or 3-ethoxy-2-hydroxybenzaldehyde and 1,2 diamine-2-methylpropane, to yield at the dianionic hexadentate Schiff base ligands H 2 L n (H 2 L 1 , H 2 L 2 respectively). The ligands have been characterised by elemental analysis, IR, 1 H and 13 C NMR spectroscopies and mass spectrometry (ES). The crystal structure of the two ligands was solved by X-ray crystallography, revealing its ability to bind metal centres.

Molecules

Condensation of 2-hydroxybenzaldehyde (salicylaldehyde) or 2-hydroxy-1-naphthaldehyde with 2-ethylaniline yields the Schiff base compound of (E)-2-(((2-ethylphenyl)imino)methyl)phenol (HL1) or (E)-1-(((2-ethylphenyl)imino)methyl)naphthalen-2-ol (HL2), which in turn react with the dinuclear complex of [Rh(η4-cod)(µ-O2CCH3)]2 (cod = cycloocta-1,5-diene) to afford the mononuclear (η4-cod){(E)-2-(((2-ethylphenyl)imino)methyl)phenolato-κ2N,O}rhodium(I), [Rh(η4-cod)(L1)] (1) or (η4-cod){(E)-1-(((2-ethylphenyl)imino)methyl)naphthalen-2-olato-κ2N,O}rhodium(I), [Rh(η4-cod)(L2)] (2) (L1 or L2 = deprotonated Schiff base ligand). The X-ray structure determination revealed that the HL2 exists in the solid state not as the usual (imine)N···H-O(phenol) form (enolamine form) but as the zwitterionic (imine)N-H+···–O(phenol) form (ketoamine form). 1H NMR spectra for HL2 in different solvents demonstrated the existence of keto-enol tautomerism (i.e., keto ⇆ enol equilibrium) in solution. The structure...

Food Science and Quality Management, 2018

A novel imine ligand TBTM [N,N'-(2,3,5,6-tetramethyl-1,4-phenylene)bis (1-(thiophen-2-yl)methanimine)] which has not been described in the literature Previously was synthesized by the condensation reaction of 2,3,5,6-tetramethylbenzene-1,4-diamine(TMBA)with thiophene-2-carbaldehyde (ThCA) then it was investigated using the density functional theory (DFT/B3LYP(6-311++ G(2d)) by finding the optimal structures for reacting and resulting compounds and also the calculation of cohesion and reaction energies in addition to the thermodynamic properties of these compounds.The calculations of the characterized thermodynamic functions for this reaction showed that the reaction is endothermic and It is found that the molar ratio of reaction is 1: 2. The analyzing of MO's energies, especially the energies of HOMO and LUMO of the reacting and resulting compounds showed that the formation reaction of this compound is not spontaneously. It is necessary to use a catalyst (as heat or chemi...

Synthetic Communications, 2001

Acta Crystallographica Section E Structure Reports Online, 2009

In the title compound, C32H28N2·CH2Cl2, the complete Schiff base and solvent molecules are both generated by crystallographic twofold axes, with the two C atoms of the former and the C atom of the latter lying on the rotation axis. The central benzene ring is substituted with two chiral groups including imine functionalities, with the common E configuration. The dihedral angle between the central benzene ring and the terminal naphthalene ring is 45.42 (9)° and that between the two naphthalene rings is 89.16 (8)°. The conformation of the Schiff base allows solvent molecules to fill the voids in the crystal, affording a stable 1:1 solvate, but the solvent interacts poorly with the Schiff base, as reflected by its rather high displacement parameters.

gazi university journal of science, 2017

Schiff base titled as 2-((2-methoxybenzylidene)amino)-6-methyl-4,5,6,7-tetrahydrobenzo[b] thiophene-3-carbonitrile was obtained by using amine;2-amino-6-methyl-4,5,6,7-tetrahydro benzo[b]thiophene-3-carbonitrile and 2-methoxybenzaldehyde. Imine compound was characterized by using elemental analysis, FTIR, NMR ( 13 C-APT, 1 H) techniques and X ray diffraction analysis. X-ray studies reveal that molecule was singly crystallized in triclinic crystal system with space group P-1. The optimized structure, chemical shifts ( 1 H and 13 C NMR) and geometrical parameters (bond lenghts, bond angles and torsion angles) of Schiff base were obtained by DFT method with B3LYP/ 6-311+G(2d,p) basis set in Gaussian 09W software program . The calculated NMR shifts and geometrical parameters were compared with the experimental results. The f rontier molecular orbitals (FMOs) and energy levels were also determined by this quantum set.