Experimental and computational studies on copper(II) Schiff base complex derived from 4-acetyl-3-methyl-1-phenyl-2-pyrazolin-5-one

被引：4

作者：

Esfahani, Maryam Hasanzadeh ^{[1
,2
]}

Fallah, Nasrin ^{[3
]}

Iranmanesh, Hasti E. ^{[3
]}

Beves, Jonathan E.

Behzad, Mahdi ^{[1
]}

机构：

[1] Semnan Univ, Fac Chem, Semnan 19111, Iran

[2] Islamic Azad Univ, Dept Chem, Sci & Res Branch, Tehran, Iran

[3] UNSW Sydney, Sch Chem, Sydney, Australia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2022年 / 1257卷

关键词：

DFT; Hirshfeld surface analysis; Pyrazolone; Schiff base; INTERMOLECULAR INTERACTIONS; TAUTOMERISM; DERIVATIVES; POLYMERS; LIGANDS;

D O I：

10.1016/j.molstruc.2022.132626

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new tetradentate N2O2 type Schiff-base ligand (H2L) was synthesized from the condensation of 4acetyl-3-methyl-1-phenyl-2-pyrazoline-5-one with 2,2-dimethyl-1,3-propanediamine. The corresponding Cu(II) complex (CuL) was also synthesized. The ligand and the complex were characterized by FTIR and UV-Vis spectroscopy and elemental analysis. H-1-and C-13 NMR spectra of the ligand and X-ray crystal structure of the complex were obtained. The main non-covalent intermolecular interactions were studied by Hirshfeld surface analysis and finger print plots. Due to the different structural possibility including imine-one, amine-ol, and amine-one forms for H2L compound, their conformational and geometrical aspects were investigated computationally by DFT/ M06-2X-6-311 + G(d,p) methods. The computational results suggested that the amine-one is the most favorable tautomeric form.(C) 2022 Elsevier B.V. All rights reserved.

引用

页数：9

共 52 条

[1] Structural tautomerism of 4-acylpyrazolone schiff bases and crystal structure of 5-methyl-2-phenyl-4-{1-[(pyridin-2-ylmethyl)-amino]-ethylidene}-2,4-dihydro-pyrazol-3-one [J].

Amarasekara, A. S. ;

Owereh, O. S. ;

Lyssenko, K. A. ;

Timofeeva, T. V. .

JOURNAL OF STRUCTURAL CHEMISTRY, 2009, 50 (06) :1159-1165

[2] Synthesis of Symmetric Bridged Bis-Pyrazolone Based Metal Complex Acid Dyes and their Applications on Leather [J].

Ayaz, Muhammad ;

Ali, Farman ;

Saeed, Aamer ;

Khurshid, Asma ;

Shabir, Ghulam ;

Ahmad, Tanveer ;

Kazmi, Syed Asad Raza ;

Khan, Hassan Ali .

JOURNAL OF FLUORESCENCE, 2018, 28 (05) :1181-1193

[3] A coumarin-pyrazolone based fluorescent probe for selective colorimetric and fluorimetric fluoride detection: Synthesis, spectroscopic properties and DFT calculations [J].

Babur, Banu ;

Seferoglu, Nurgul ;

Seferoglu, Zeynel .

JOURNAL OF MOLECULAR STRUCTURE, 2018, 1161 :218-225

[4] A combined experimental and computational study on the interaction of nitrogen mustards with DNA [J].

Bonsaii, Mahyar ;

Gholivand, Khodayar ;

Abdi, Khosrou ;

Valmoozi, Ali Asghar Ebrahimi ;

Khosravi, Morteza .

MEDCHEMCOMM, 2016, 7 (10) :2003-2015

[5]

Bruker APEX3, 2016, SAINT-Plus and SADABS

[6] Synthesis, Characterization, and Antitumor Activity of Water-Soluble (Arene)ruthenium(II) Derivatives of 1,3-Dimethyl-4-acylpyrazolon-5-ato Ligands. First Example of Ru(arene)(ligand) Antitumor Species Involving Simultaneous Ru-N7(guanine) Bonding and Ligand Intercalation to DNA [J].

Caruso, Francesco ;

Monti, Elena ;

Matthews, Julian ;

Rossi, Miriam ;

Gariboldi, Marzia Bruna ;

Pettinari, Claudio ;

Pettinari, Riccardo ;

Marchetti, Fabio .

INORGANIC CHEMISTRY, 2014, 53 (07) :3668-3677

[7] Coordination modes of 5-pyrazolones:: A solid-state overview [J].

Casas, Jose S. ;

Garcia-Tasende, Maria S. ;

Sanchez, Agustin ;

Sordo, Jose ;

Touceda, Angeles .

COORDINATION CHEMISTRY REVIEWS, 2007, 251 (11-12) :1561-1589

[8] Asymmetric Chlorination of 4-Substituted Pyrazolones Catalyzed by Chiral Copper Complexes [J].

Chen, Xue-Yang ;

Jiang, Zhen-Hui ;

Ju, Wan-Zhen ;

Yin, Hao ;

Qi, Suo-Suo ;

Chu, Ming-Ming ;

Wang, Yi-Feng .

SYNLETT, 2020, 31 (13) :1318-1322

[9] OLEX2: a complete structure solution, refinement and analysis program [J].

Dolomanov, Oleg V. ;

Bourhis, Luc J. ;

Gildea, Richard J. ;

Howard, Judith A. K. ;

Puschmann, Horst .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341

[10] Synthesis and characterization of a series of acylpyrazolone transition metal complexes: Crystal structures and catalytic performance in the epoxidation of cyclooctene [J].

Esfahani, Maryam Hasanzadeh ;

Behzad, Mahdi ;

Dusek, Michal ;

Kucerakova, Monika .

INORGANICA CHIMICA ACTA, 2020, 508

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