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Synthesis, solvatochromism and crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H -1,2,4-triazine-3-thione.

Rezaei B, Fazlollahi M - Chem Cent J (2013)

Bottom Line: It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions.While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm.Thus, the title compound showed positive solvatochromic behavior.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Lorestan University, Khorramabad, Iran.

ABSTRACT

Background: For the development of properties in molecular crystals, such as electrical conductivities, magnetic properties, or non-linear optical properties, not only the electronic properties of molecules themselves matter, but also the molecular arrangements in the crystals are very important. Therefore, the design of the crystal structures and the control of molecular arrangements have attracted much attention in recent years. Among various ligands, triazine moieties have been especially interesting because of their biological, pharmacological and medicinal properties.

Results: Crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione is Monoclinic, which consists of space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4, R1 = 0.0371 and wR2 = 0.1008 with 2456 reflections (I > 2σ(I)). Intermolecular H bonds between NH groups are acting as donors and S atoms as acceptors. There are also shorted face-to-face as well as edge to face π-π stacking interactions between the parallel aromatic rings. The behavior of solvatochromic of the mentioned compound that involved interhydrogen bonding was investigated by studying its electronic absorption spectra in pure organic solvents of different characters.

Conclusions: The crystal structure of C16H15N3OS, shows the expected face-to-face π-π stacking interactions between aromatic rings of the neighbor chains in this compound. The centroid-centroid distance between the aromatic rings is 3.325 Å. It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions. The solvatochromic behavior of the title compound was also investigated by studying its spectra in a selection of different organic solvents. While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm. Thus, the title compound showed positive solvatochromic behavior.

No MeSH data available.


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The synthesis procedure of the title compound.
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C1: The synthesis procedure of the title compound.

Mentions: The title compound was prepared by reaction of a solution of thiosemicarbazide (15 mmol) in methanol with a solution of HCl (30 cm3, 2 M), 1 cm3 of concentrated HCl and a solution of benzyl (15 mmol) in methanol at room temperature to form 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione [6]. M. P. = 232-233°C, Scheme 1, The branched tube method was used for the preparation of suitable single crystals [4]. The title compound (0.2 g) was placed in one arm of a branched tube, acetonitrile was carefully added to fill both arms, the tube sealed and the compound containing arm immersed in a bath at 60°C, while the other one was at ambient temperature. After 7 days, the suitable crystals for X-ray analysis of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione were deposited in the cooler arm which was filtered off, washed with ether, and air dried.


Synthesis, solvatochromism and crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H -1,2,4-triazine-3-thione.

Rezaei B, Fazlollahi M - Chem Cent J (2013)

The synthesis procedure of the title compound.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3750551&req=5

C1: The synthesis procedure of the title compound.
Mentions: The title compound was prepared by reaction of a solution of thiosemicarbazide (15 mmol) in methanol with a solution of HCl (30 cm3, 2 M), 1 cm3 of concentrated HCl and a solution of benzyl (15 mmol) in methanol at room temperature to form 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione [6]. M. P. = 232-233°C, Scheme 1, The branched tube method was used for the preparation of suitable single crystals [4]. The title compound (0.2 g) was placed in one arm of a branched tube, acetonitrile was carefully added to fill both arms, the tube sealed and the compound containing arm immersed in a bath at 60°C, while the other one was at ambient temperature. After 7 days, the suitable crystals for X-ray analysis of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione were deposited in the cooler arm which was filtered off, washed with ether, and air dried.

Bottom Line: It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions.While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm.Thus, the title compound showed positive solvatochromic behavior.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Lorestan University, Khorramabad, Iran.

ABSTRACT

Background: For the development of properties in molecular crystals, such as electrical conductivities, magnetic properties, or non-linear optical properties, not only the electronic properties of molecules themselves matter, but also the molecular arrangements in the crystals are very important. Therefore, the design of the crystal structures and the control of molecular arrangements have attracted much attention in recent years. Among various ligands, triazine moieties have been especially interesting because of their biological, pharmacological and medicinal properties.

Results: Crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione is Monoclinic, which consists of space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4, R1 = 0.0371 and wR2 = 0.1008 with 2456 reflections (I > 2σ(I)). Intermolecular H bonds between NH groups are acting as donors and S atoms as acceptors. There are also shorted face-to-face as well as edge to face π-π stacking interactions between the parallel aromatic rings. The behavior of solvatochromic of the mentioned compound that involved interhydrogen bonding was investigated by studying its electronic absorption spectra in pure organic solvents of different characters.

Conclusions: The crystal structure of C16H15N3OS, shows the expected face-to-face π-π stacking interactions between aromatic rings of the neighbor chains in this compound. The centroid-centroid distance between the aromatic rings is 3.325 Å. It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions. The solvatochromic behavior of the title compound was also investigated by studying its spectra in a selection of different organic solvents. While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π-π* transition, was red shifted by 13 nm. Thus, the title compound showed positive solvatochromic behavior.

No MeSH data available.


Related in: MedlinePlus