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Synthesis, spectroscopic (UV-vis and GIAO NMR), crystallographic and theoretical studies of triazine heterocyclic derivatives

Synthesis, spectroscopic (UV-vis and GIAO NMR), crystallographic and theoretical studies of triazine heterocyclic derivatives
Synthesis, spectroscopic (UV-vis and GIAO NMR), crystallographic and theoretical studies of triazine heterocyclic derivatives
This work presents the synthesis and characterization of triazine heterocyclic derivatives. The spectroscopic properties like nuclear magnetic resonance [NMR, (1H and 13C)] were recorded in CDCl3 solution and Ultraviolet-Visible (UV-vis) absorption spectrums of compounds, 5,6-diphenyl-[1,2,4]triazin-3-ylamine (1), (5,6-diphenyl-[1,2,4]triazin-3-yl)-hydrazine (2) and 5,6-diphenyl-4H-[1,2,4] triazine-3-thione (3), were recorded in the range of 200-800 nm, using chloroform as base solvent. Molecular geometry of compounds with triazine heterocyclic derivative in the ground state have been calculated using the density functional theory (DFT) with 6-31G(d,p) basis set and compared with the X-ray experimental data. The calculated results show that the optimized geometry can well reproduce the crystal structures. Total static dipole moment (?), the average linear polarizability (?) and the first hyperpolarizability (?) values of the investigated molecules have been computed using the same methods. The energetic behavior of compounds in solvent media has been examined using B3LYP method with the 6-31G(d,p) basis set by applying the polarizable continuum model (PCM). The total energy of compounds decreases with increasing polarity of the solvent. Frontier molecular orbitals and the molecular electrostatic potential (MEP), 1H-NMR, and 13C-NMR of three triazine derivatives were investigated using theoretical calculations. The linear polarizabilities and first hyperpolarizabilities of the studied molecules indicate that the compounds 1-3 can be used as a good nonlinear optical material (NLO). Isotropic chemical shifts were calculated using the gauge-invariant atomic orbital (GIAO) method. Comparison of the NMR chemical shifts, absorption wavelengths with the experimental values revealed that DFT and time dependent-density functional theory (TD-DFT) method produce generally closer to good results.
1, 2, 4-Triazine, crystal structure, DFT, non-linear optical properties, HOMO-LUMO, MEP
0022-2860
1-29
Khan, Salman A.
dbab728a-b70c-43c5-9cc4-1e3114a1e57c
Obaid, Abdullah Y.
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Al-Harbi, Laila M.
96de26ae-4402-4994-b15a-21a678d95638
Arshad, Muhammad Nadeem
c3a8a663-09b1-473a-8456-ec1595f4702d
Şahin, Onur
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Ersanlı, Cem Cüneyt
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Abdel-Rehman, R.M.
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Asiri, Abdullah M.
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Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Khan, Salman A.
dbab728a-b70c-43c5-9cc4-1e3114a1e57c
Obaid, Abdullah Y.
c33c6513-31bb-4e03-8baa-f8b41d5e9e0b
Al-Harbi, Laila M.
96de26ae-4402-4994-b15a-21a678d95638
Arshad, Muhammad Nadeem
c3a8a663-09b1-473a-8456-ec1595f4702d
Şahin, Onur
27853670-f14a-4416-9cbb-84ffb45720c2
Ersanlı, Cem Cüneyt
6303856d-ba28-421a-855a-8d6f2a04f5f4
Abdel-Rehman, R.M.
8a0e619f-ce00-43ac-a09a-80b0f259444e
Asiri, Abdullah M.
e7846d10-8173-451e-9361-efe848cd10c0
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Khan, Salman A., Obaid, Abdullah Y., Al-Harbi, Laila M., Arshad, Muhammad Nadeem, Şahin, Onur, Ersanlı, Cem Cüneyt, Abdel-Rehman, R.M., Asiri, Abdullah M. and Hursthouse, Michael B. (2015) Synthesis, spectroscopic (UV-vis and GIAO NMR), crystallographic and theoretical studies of triazine heterocyclic derivatives. Journal of Molecular Structure, 1-29. (doi:10.1016/j.molstruc.2015.04.036).

Record type: Article

Abstract

This work presents the synthesis and characterization of triazine heterocyclic derivatives. The spectroscopic properties like nuclear magnetic resonance [NMR, (1H and 13C)] were recorded in CDCl3 solution and Ultraviolet-Visible (UV-vis) absorption spectrums of compounds, 5,6-diphenyl-[1,2,4]triazin-3-ylamine (1), (5,6-diphenyl-[1,2,4]triazin-3-yl)-hydrazine (2) and 5,6-diphenyl-4H-[1,2,4] triazine-3-thione (3), were recorded in the range of 200-800 nm, using chloroform as base solvent. Molecular geometry of compounds with triazine heterocyclic derivative in the ground state have been calculated using the density functional theory (DFT) with 6-31G(d,p) basis set and compared with the X-ray experimental data. The calculated results show that the optimized geometry can well reproduce the crystal structures. Total static dipole moment (?), the average linear polarizability (?) and the first hyperpolarizability (?) values of the investigated molecules have been computed using the same methods. The energetic behavior of compounds in solvent media has been examined using B3LYP method with the 6-31G(d,p) basis set by applying the polarizable continuum model (PCM). The total energy of compounds decreases with increasing polarity of the solvent. Frontier molecular orbitals and the molecular electrostatic potential (MEP), 1H-NMR, and 13C-NMR of three triazine derivatives were investigated using theoretical calculations. The linear polarizabilities and first hyperpolarizabilities of the studied molecules indicate that the compounds 1-3 can be used as a good nonlinear optical material (NLO). Isotropic chemical shifts were calculated using the gauge-invariant atomic orbital (GIAO) method. Comparison of the NMR chemical shifts, absorption wavelengths with the experimental values revealed that DFT and time dependent-density functional theory (TD-DFT) method produce generally closer to good results.

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Accepted/In Press date: 27 April 2015
e-pub ahead of print date: 6 May 2015
Keywords: 1, 2, 4-Triazine, crystal structure, DFT, non-linear optical properties, HOMO-LUMO, MEP
Organisations: Chemistry

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Local EPrints ID: 376919
URI: http://eprints.soton.ac.uk/id/eprint/376919
ISSN: 0022-2860
PURE UUID: 7a9bd424-f41f-451b-bc0c-42a71f3618a0

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Date deposited: 13 May 2015 08:35
Last modified: 12 Nov 2019 06:46

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Contributors

Author: Salman A. Khan
Author: Abdullah Y. Obaid
Author: Laila M. Al-Harbi
Author: Muhammad Nadeem Arshad
Author: Onur Şahin
Author: Cem Cüneyt Ersanlı
Author: R.M. Abdel-Rehman
Author: Abdullah M. Asiri

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