6533b821fe1ef96bd127c0a7
RESEARCH PRODUCT
Extending the halogen-bonded supramolecular synthon concept to 1,3,4-oxadiazole derivatives
Duncan W. BruceCatalina Ruiz-pérezSergio LealEsteban Vöhringer-martinezP. I. HidalgoClaudio A. JiménezJorge PasánJorge PasánBárbara Herrerasubject
010405 organic chemistryStereochemistrySynthonSupramolecular chemistryOxadiazoleGeneral ChemistryCrystal structureElectronic structure010402 general chemistryCondensed Matter PhysicsRing (chemistry)01 natural sciences0104 chemical scienceschemistry.chemical_compoundCrystallographychemistryHalogenPyridineGeneral Materials Sciencedescription
A series of five crystal structures of 1:1 halogen-bonded complexes were obtained from 4-[5-(4-alkoxyphenyl)-1,3,4-oxadiazole-2-yl]pyridine and 1,3,5-trifluorotriiodobenzene. Electronic structure calculations show that the N(oxadiazole)⋯I interaction in the new synthon is as strong as the classic N(pyridine)⋯I interaction. Oxygen to sulfur atom subsitution on the oxadiazole ring results in a different supramolecular packing where the N(pyridine)⋯I interaction is favored, which could be rationalized by the changes in the molecular electrostatic potential predicted from the theoretical calculations.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-01-01 | CrystEngComm |