2,5-Bis(3-pyridyl)-1,3,4-thiadiazole

Niu, Cao‐Yuan; Hou, Shicong; Wan, Xin-Sheng; Kou, Chun-Hong; Feng, Cao-Ling

doi:10.1107/s1600536807014432

Cited by 2 publications

(1 citation statement)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All these chemicals were used as received. The 3-BPTD has both cis and trans isomers [43,44]. As shown in Figure 1, we only considered the cis isomer of 3-BPTD in this work.…”

Section: Experimental Methodsmentioning

confidence: 99%

Tuning of the Electrostatic Potentials on the Surface of the Sulfur Atom in Organic Molecules: Theoretical Design and Experimental Assessment

Wang

2023

Molecules

View full text Add to dashboard Cite

Noncovalent sulfur interactions are ubiquitous and play important roles in medicinal chemistry and organic optoelectronic materials. Quantum chemical calculations predicted that the electrostatic potentials on the surface of the sulfur atom in organic molecules could be tuned through the through-space effects of suitable substituents. This makes it possible to design different types of noncovalent sulfur interactions. The theoretical design was further confirmed by X-ray crystallographic experiments. The sulfur atom acts as the halogen atom acceptor to form the halogen bond in the cocrystal between 2,5-bis(2-pyridyl)-1,3,4-thiadiazole and 1,4-diiodotetrafluorobenzene, whereas it acts as the chalcogen atom donor to form the chalcogen bond in the cocrystal between 2,5-bis(3-pyridyl)-1,3,4-thiadiazole and 1,3,5-trifluoro-2,4,6-triiodobenzene.

show abstract

“…All these chemicals were used as received. The 3-BPTD has both cis and trans isomers [43,44]. As shown in Figure 1, we only considered the cis isomer of 3-BPTD in this work.…”

Section: Experimental Methodsmentioning

confidence: 99%

Tuning of the Electrostatic Potentials on the Surface of the Sulfur Atom in Organic Molecules: Theoretical Design and Experimental Assessment

Wang

2023

Molecules

View full text Add to dashboard Cite

show abstract

Crystal structure of cis-2,5-bis(3-pyridyl)-1,3,4-thiadiazole, C12H8N4S

Niu¹,

Ning²,

Dang³

et al. 2008

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

Source of material 2,5-Bis(3-pyridyl)-1,3,4-thiadiazole was prepared similarly to the literature procedure [1]. A mixture of nickel acetate monohydrate (0.026 g, 0.1 mmol), 2,5-bis(3-pyridyl)-1,3,4-thiadiazole (0.024 g, 0.1mmol), 2,2-dipy-4,4-bicarboxylic acid (0.012 g, 0.05 mmol), ethanol (5 ml) and 25 % ammonia water (3 ml) was sealed in a 15 ml Teflon-lined stainless steel reactor. The reactor was heated in an oven at 180°C for 72 hours and then cooled to room temperature at a rate of 10°C/h. Yellow needlelike crystals were obtained. DiscussionThe crystal structure of trans-2,5-bis(3-pyridyl)-1,3,4-thiadiazole has been already reported [2], and the structures of its other isomers (4-pyridyl or 2-pyridyl-1,3,4-thiadiazole) have been previously X-ray characterized [3][4][5]. The two pyridyl rings within each molecule (figure, top) form a dihedral angle of 20.78(5)°with the mean plane difined by the central thiadiazole ring, which is larger than those in the trans-2,5-bis(3-pyridyl)-1,3,4-thiadiazole molecule. There is a 2-fold axis through the middle point of the N-N bond in the thiadiazole ring and the sulfur atom. There are C−H···N hydrogen bonds between cis-2,5-bis(3-pyridyl)-1,3,4-thiadiazole molecules with the distance of H···A about 2.95 Å (figure, middle). Another kind of intermolecular interaction is C−H···p interactions (figure, bottom). The distance between hydrogen atom and the center of aromatic pyridyl ring is about 2.8 Å. Furthermore, it is interesting that cis-and trans -2,5-bis(3-pyridyl)-1,3,4-thiadiazole are synthesized under very different conditions. This indicates that factors like temperature, metal ions, other organic compounds in the reaction mixture may affect the conformation of the organic molecules.

show abstract

2,5-Bis(3-pyridyl)-1,3,4-thiadiazole

Abstract: The title molecule, C12H8N4S, possesses antibacterial properties and is a potential ligand for metal complexes. The dihedral angles between the pyridyl rings and the central thiadiazole ring are less than 10°.

Cited by 2 publications

References 4 publications

Tuning of the Electrostatic Potentials on the Surface of the Sulfur Atom in Organic Molecules: Theoretical Design and Experimental Assessment

Tuning of the Electrostatic Potentials on the Surface of the Sulfur Atom in Organic Molecules: Theoretical Design and Experimental Assessment

Crystal structure of cis-2,5-bis(3-pyridyl)-1,3,4-thiadiazole, C12H8N4S

Contact Info

Product

Resources

About