A series of cocrystals of halogen bond donors 1,4-diiodotetrafluorobenzene (-FDIB) and tetraiodoethylene (TIE) with five aromatic heterocyclic diazine mono--oxides based on pyrazine, tetramethylpyrazine, quinoxaline, phenazine, and pyrimidine as halogen bonding acceptors were studied. Structural analysis of the mono--oxides allows comparison of the competitive occurrence of N···I vs O···I interactions and the relative strength and directionality of these two types of interactions. Of the aromatic heterocyclic diazine mono--oxide organoiodine cocrystals examined, six exhibited 1:1 stoichiometry, forming chains that utilized both N···I and O···I interactions.
View Article and Find Full Text PDFThrough the combination of heterocyclic thiones with variation in the identity of the heterocyclic elements, namely, imidazolidine-2-thione, 2-mercaptobenzimidazole, 2-mercapto-5-methylbenzimidazole, 2-mercaptobenzoxazole, and 2-mercaptobenzothiazole with the common halogen-bond donors 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene, 1,3,5-trifluorotriiodobenzene, and tetraiodoethylene, a series of 18 new crystalline structures were characterized. In most cases, N-H..
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View Article and Find Full Text PDFActa Crystallogr C Struct Chem
October 2021
By varying the halogen-bond-donor molecule, 11 new halogen-bonding cocrystals involving thiourea or 1,3-dimethylthiourea were obtained, namely, 1,3-dimethylthiourea-1,2-diiodo-3,4,5,6-tetrafluorobenzene (1/1), CFI·CHNS, 1, thiourea-1,3-diiodo-2,4,5,6-tetrafluorobenzene (1/1), CFI·CHNS, 2, 1,3-dimethylthiourea-1,3-diiodo-2,4,5,6-tetrafluorobenzene (1/1), CFI·CHNS, 3, 1,3-dimethylthiourea-1,3-diiodo-2,4,5,6-tetrafluorobenzene-methanol (1/1/1), CFI·CHNS·CHO, 4, 1,3-dimethylthiourea-1,3-diiodo-2,4,5,6-tetrafluorobenzene-ethanol (1/1/1), CFI·CHNS·CHO, 5, 1,3-dimethylthiourea-1,4-diiodo-2,3,5,6-tetrafluorobenzene (1/1), CFI·CHNS, 6, 1,3-dimethylthiourea-1,3,5-trifluoro-2,4,6-triiodobenzene (1/1), CFI·CHNS, 7, 1,3-dimethylthiourea-1,1,2,2-tetraiodoethene (1/1), CHNS·CI, 8, [(dimethylamino)methylidene](1,2,2-triiodoethenyl)sulfonium iodide-1,1,2,2-tetraiodoethene-acetone (1/1/1), CHINS·I·CHO·CI, 9, 2-amino-4-methyl-1,3-thiazol-3-ium iodide-1,1,2,2-tetraiodoethene (2/3), 2CHNS·2I·3CI, 10, and 4,4-dimethyl-4H-1,3,5-thiadiazine-3,5-diium diiodide-1,1,2,2-tetraiodoethene (2/3), 2CHNS·4I·3CI, 11. When utilizing the common halogen-bond-donor molecules 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene, as well as 1,3,5-trifluoro-2,4,6-triiodobenzene, bifurcated I..
View Article and Find Full Text PDFThrough variations in reaction solvent and stoichiometry, a series of S-diiodine adducts of 1,3- and 1,4-dithiane were isolated by direct reaction of the dithianes with molecular diiodine in solution. In the case of 1,3-dithiane, variations in reaction solvent yielded both the equatorial and the axial isomers of S-diiodo-1,3-dithiane, and their solution thermodynamics were further studied via DFT. Additionally, S,S'-bis(diiodo)-1,3-dithiane was also isolated.
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