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Article

Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study

by
Muhammad Nadeem Arshad
1,*,
Aisha Bibi
2,
Tariq Mahmood
2,*,
Abdullah M. Asiri
1,3 and
Khurshid Ayub
2,4
1
Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
2
Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, 22060 Abbottabad, Pakistan
3
Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
4
Department of Chemistry, College of Science, King Faisal University, Al-Hafouf 31982, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Molecules 2015, 20(4), 5851-5874; https://doi.org/10.3390/molecules20045851
Submission received: 14 February 2015 / Revised: 18 March 2015 / Accepted: 23 March 2015 / Published: 3 April 2015
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

We report here a comparative theoretical and experimental study of four triazine-based hydrazone derivatives. The hydrazones are synthesized by a three step process from commercially available benzil and thiosemicarbazide. The structures of all compounds were determined by using the UV-Vis., FT-IR, NMR (1H and 13C) spectroscopic techniques and finally confirmed unequivocally by single crystal X-ray diffraction analysis. Experimental geometric parameters and spectroscopic properties of the triazine based hydrazones are compared with those obtained from density functional theory (DFT) studies. The model developed here comprises of geometry optimization at B3LYP/6-31G (d, p) level of DFT. Optimized geometric parameters of all four compounds showed excellent correlations with the results obtained from X-ray diffraction studies. The vibrational spectra show nice correlations with the experimental IR spectra. Moreover, the simulated absorption spectra also agree well with experimental results (within 10–20 nm). The molecular electrostatic potential (MEP) mapped over the entire stabilized geometries of the compounds indicated their chemical reactivates. Furthermore, frontier molecular orbital (electronic properties) and first hyperpolarizability (nonlinear optical response) were also computed at the B3LYP/6-31G (d, p) level of theory.
Keywords: triazine; hydrazone; X-ray; DFT; MEP; first hyperpolarizability triazine; hydrazone; X-ray; DFT; MEP; first hyperpolarizability
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MDPI and ACS Style

Arshad, M.N.; Bibi, A.; Mahmood, T.; Asiri, A.M.; Ayub, K. Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study. Molecules 2015, 20, 5851-5874. https://doi.org/10.3390/molecules20045851

AMA Style

Arshad MN, Bibi A, Mahmood T, Asiri AM, Ayub K. Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study. Molecules. 2015; 20(4):5851-5874. https://doi.org/10.3390/molecules20045851

Chicago/Turabian Style

Arshad, Muhammad Nadeem, Aisha Bibi, Tariq Mahmood, Abdullah M. Asiri, and Khurshid Ayub. 2015. "Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study" Molecules 20, no. 4: 5851-5874. https://doi.org/10.3390/molecules20045851

APA Style

Arshad, M. N., Bibi, A., Mahmood, T., Asiri, A. M., & Ayub, K. (2015). Synthesis, Crystal Structures and Spectroscopic Properties of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study. Molecules, 20(4), 5851-5874. https://doi.org/10.3390/molecules20045851

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