A Combined Theoretical Investigation and X-Ray Study of 2-(4-Dimethylamino)benzylideneamino)-3-aminomaleonitrile



In the present work a Schiff base ligand 2-(4-(dimethylamino)benzylideneamino)-3-aminomaleonitrile was prepared via condensation of diaminomaleonitrile and 4-(dimethylamino)benzaldehyde under reflux. This compound was characterized by elemental analysis, FT-IR spectroscopy and single crystal X-ray diffraction. The ground state properties of the title molecule have been calculated employing DFT/B3LYP level of the theory using the 6-31G (d, p) basis set. The first static hyperpolarizability of this compound is found to be 26.76´10-30 (esu). So this imino compound is a suitable molecule for optical nonlinearity. Calculated bond lengths and bond angles are in good agreement with X-ray data.



DFT/B3LYP, 6-31G (d, p), hyperpolarizability, nonlinear optical property (NLO), theoretical study

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H Schiff. Mittheilungen Aus Dem Universitat Slaboratorium in Pisa: Eine Neue Reihe Organischer Basen. Justus Liebigs. Ann. Chem. 1864; 131, 118-9.

DN Dhar and CL Taploo. Schiff bases and their applications. J. Sci. Ind. Res. 1982; 41, 501-6.

PK Sasmal, S Saha, R Majumdar, RR Dighe and AR Chakravarty. Oxovanadium(IV)-Based Near-IR PDT agents: design to biological evaluation. Chem. Commun. 2009; 13, 1703-5.

M Roy, T Bhowmick, R Santhanagopal, S Ramakumar and AR Chakravarty. Photo-induced double-strand DNA and site-specific protein cleavage activity of L-histidine (m-oxo)Diiron(III) complexes of heterocyclic bases. Dalton Trans. 2009; 24, 4671-82.

MSA Begum, S Saha, M Nethaji and AR Chakravarty. Iron(III) Schiff base complexes activity. J. Inorg. Biochem. 2010; 104, 477-84.

CN Bhardwaj and VR Singh. Synthesis and characterization of Thallium(I) complexes of biologically active benzothiazolines. Indian J. Chem. 1994; 33A, 423-5.

TD Bharamagouclar, MA Pujar and AR Alagawadi. Biological activity of Schiff base and their metal complexes. Curr. Sci. 1987; 56, 889-90.

MD Deshmukh and AG Doshi. Synthesis of Schiff bases and their applications. Orient. J. Chem. 1995; 11, 86-96.

M Tumer, H Koksal, S Serin and M Digrak. Antimicrobial study of mononuclear and binuclear mixed ligand Cu (II) complexes, derived from 1, 10-phenanthroline. Trans. Met. Chem. 1999; 24, 13-7.

I Sheikhshoaie, A Rezaeifard, N Monadi and S Kaafi. A novel tridentate Schiff base dioxo-molybdenum(VI) complex: Synthesis, crystal structure and catalytic performance in green oxidation of sulfides by urea hydrogen peroxide. Polyhedron 2009; 28, 733-8.

M Hatefi, M Moghadam, V Mirkhani and I Sheikhshoaei. Silica supported Ru(salophen)Cl: An efficient and robust heterogeneous catalyst for epoxidation of alkenes with sodium periodate. Polyhedron 2010; 29, 2953-8.

A Nishinaga, T Yamada, H Fujisawa and K Ishizaki. Catalysis by cobalt Schiff base complexes in the oxygenation of alkenes on the mechanism of ketonization. J. Mol. Catal. 1988; 48, 249-64.

Z Xi, W Liu, G Cao, W Du, J Huang, K Cai and H Guo. Catalytic oxidation of naphthol by metalloporphyrins. Cuihau Xuebao 1986; 7, 357-63.

A Rezaeifard, I Sheikhshoaie, N Monadi and H Stoeckli-Evans. Synthesis, crystal structure, and catalytic properties of novel dioxidomolybdenum (VI) complexes with tridentate Schiff base ligands in the biomimetic and highly selective oxygenation of alkenes and sulfides. Eur. J. Inorg. Chem. 2010; 5, 799-806.

YD Zhao, DW Pang, Z Zong, JK Cheng, ZF Luo, CJ Feng, HY Shen and XC Zhung. Electochemical studies of antitumor drugs, fundamental electrochemical characteristics of an iron(III) complex and interaction with DNA. Huaxe Xuebao 1988; 56, 178-83.

RW Hay, PR Norman and F McLaren. Cobalt (II) and alkylcobalt(III) complexes of N,N′-bis(2-thioformyl-2-phenylvinyl)trimethylenediamine. A cobalt(II) oxygen carrier. Inorg. Chim. Acta 1980; 44, 125-7.

G Pascal, FA Lacroix, M Isabelle and N Keitaro. Synthesis, Crystal structures and molecular hyperpolarizabilities of a new Schiff base ligand, and its copper (II), nickel (II), and cobalt (II) metal complexes. Inorg. Chim. Acta 2004; 357, 3825-35.

I Sheikhshoaie and WMF Fabian. Theoretical insights into material properties of Schiff bases and related azo compounds. Curr. Org. Chem. 2009; 13, 149-71.

PN Prasad and DJ Williams. Introduction to Non-Linear Optical Effects in Molecules and Polymers. John Willy & Sons Inc., New York, 1991.

YP Tian, CY Duan, CY Zhao and XZ You. Synthesis, Crystal structure and second-order optical nonlinearity of bis(2-chlorobenzaldehyde thiosemicarbazone) Cadmium halides (CdL2X2: X=Br, I). Inorg. Chem. 1997; 36, 1247-52.

W Kohn and LJ Sham. Self-consistent equations including exchange and correlation effects. Phys. Rev. 1958; 140, A1133-8.

AD Becke. Density‐functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993; 98, 5648-52.

MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, JA Montgomery Jr., T Vreven, KN Kudin, JC Burant, JM Millam, SS Iyengar, J Tomasi, V Barone, B Mennucci, M Cossi, G Scalmani, N Rega, GA Petersson, H Nakatsuji, M Hada, M Ehara, K Toyota, R Fukuda, J Hasegawa, M Ishida, T Nakajima, Y Honda, O Kitao, H Nakai, M Klene, X Li, JE Knox, HP Hratchian, JB Cross, C Adamo, J Jaramillo, R Gomperts, RE Stratmann, O Yazyev, AJ Austin, R Cammi, C Pomelli, JW Ochterski, PY Ayala, K Morokuma, GA Voth, P Salvador, JJ Dannenberg, VG Zakrzewski, S Dapprich, AD Daniels, MC Strain, O Farkas, DK Malick, AD Rabuck, K Raghavachari, JB Foresman, JV Ortiz, Q Cui, AG Baboul, S Clifford, J Cioslowski, BB Stefanov, G Liu, A Liashenko, P Piskorz, I Komaromi, RL Martin, DJ Fox, T Keith, MA Al-Laham, CY Peng, A Nanayakkara, M Challacombe, PMW Gill, B Johnson, W Chen, MW Wong and C Gonza. Information Technology Services. University of Wollongong, Gaussian Inc., Wallingford, CT.

I Sheikhshoaie, SY Ebrahimipour and M Sheikhshoaee. Structural investigation of methanol {6-[(2-oxidopropyl)iminomethyl]phenolato}dioxidomolybdenum(VI) by X-ray crystallography and DFT calculations. Walailak J. Sci. & Tech. 2012, 9, 207-16.


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