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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Synthesis, crystal structure analysis, spectral characterization and nonlinear optical exploration of potent thiosemicarbazones based compounds: A DFT refine experimental study

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Author(s):
Jawaria, Rifat [1] ; Hussain, Mazhar [2] ; Khalid, Muhammad [1] ; Khan, Muhammad Usman [3] ; Tahir, Muhammad Nawaz [4] ; Naseer, Muhammad Moazzam [5] ; Carmo Braga, Ataualpa Albert [6] ; Shafiq, Zahid [2]
Total Authors: 8
Affiliation:
[1] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan
[2] Bahauddin Zakariya Univ, Inst Chem Sci, Multan 60800 - Pakistan
[3] Govt Coll Univ, Dept Appl Chem, Faisalabad 38000 - Pakistan
[4] Univ Sargodha, Dept Phys, Sargodha 40100 - Pakistan
[5] Quaid I Assam Univ, Dept Chem, Islamabad 45320 - Pakistan
[6] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Ave Prof Lineu Prestes 748, BR-05508000 Sao Paulo - Brazil
Total Affiliations: 6
Document type: Journal article
Source: Inorganica Chimica Acta; v. 486, p. 162-171, FEB 24 2019.
Web of Science Citations: 22
Abstract

The thiosemicarbazones have exciting biological and nonlinear optical (NLO) applications. The present study reports detail experimental and computational studies of three novel ferrocene-substituted thiosemicarbazones: (E/Z)-4-benzyl-1-(1-ferrocenylethyl)thiosemicarbazones (1), (E/Z)-4-(4-chlorobenzyl)-1-(1-ferrocenyl-ethyl) thiosemicarbazone (2) and (E/Z)-4-(2-bromo benzyl)-1-(1-ferrocenylethyl)thiosemicarbazone (3). These compounds were synthesized and resolved into their single crystal structures for the estimation of unit cells, space groups, bond angles and bond lengths. Chemical structures of 1-3 were further characterized spectroscopically employing nuclear magnetic resonance technique (1H NMR), infrared (FT-IR), mass and UV-Visible studies. Computational studies of 1-3 were performed using density functional theory (DFT) tools at M06 level of theory and 6-31 + G(d,p) basis set combination to gain the optimized geometry. A good correlation was found between experimental SC-XRD structures and DFT optimized geometries. Electronic properties including natural bond orbital (NBO) analysis, frontier molecular orbitals (FMOs) analysis, spectroscopic FT-IR data and NLO properties were calculated using same M06/6-31 + G(d,p) level of theory. NBO analysis confirmed the formation of charge separation state due to successful migration of electrons from donor to acceptor unit through pi-bridge. Global reactivity parameters were estimated using energies of FMOs which described that 1-3 are chemically hard and stable molecules. Vertical electronic transition states were calculated using time-dependent DFT (TDDFT) at same level of theory. NLO properties of 1-3 were computed 5.77, 3.48 and 8.93 times greater than the standard urea molecule respectively. Two-state model confirmed the potential of synthesized molecules as NLO candidates. (AU)

FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
Grantee:Ataualpa Albert Carmo Braga
Support Opportunities: Regular Research Grants