The preparation of 1,4,8,11-tetrabromo-5b[small alpha],6,12b[small alpha],13-tetrahydropentaleno[1,2-b:4,5-b[prime or minute]]diquinoline is described. This is a further member of the tetrahalo aryl host family, and forms crystalline lattice inclusion compounds with many guests. The X-ray structures of the allyl cyanide, 1,2,3-trichloropropane, chlorobenzene, toluene, benzene-water, methyl chloroform and carbon tetrachloride inclusion compounds are described, and compared with that of the solvent-free apohost. Although several different structural types are produced, the recently reported pi-halogen dimer (PHD) interaction plays an important role in all of these, except for that of pure (where the packing energy is the least favourable of the series).
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http://dx.doi.org/10.1039/b310638a | DOI Listing |
RSC Adv
November 2023
Biomolecular Crystallography Laboratory and DBT-Bioinformatics Center, School of Chemical and Biotechnology, SASTRA Deemed University Thanjavur 613 401 India
Two 1,3,4-oxadiazole-2-thione--Mannich derivatives, specifically 5-(4-chlorophenyl)-3-[(2-trifluoromethylphenylamino)methyl]-1,3,4-oxadiazole-2(3)-thione (1) and 5-(4-chlorophenyl)-3-[(2,5-difluorophenylamino)methyl]-1,3,4-oxadiazole-2(3)-thione (2), were synthesized and then characterized by elemental analysis and NMR (H and C) spectroscopy and the single crystal X-ray diffraction method. The formed weak intermolecular interactions in the solid-state structures of these derivatives were thoroughly investigated utilizing a variety of theoretical tools such as Hirshfeld surface analysis and quantum theory of atoms in molecules (QTAIM). Furthermore, the CLP-PIXEL and density functional theory calculations were used to study the energetics of molecular dimers.
View Article and Find Full Text PDFPhys Chem Chem Phys
July 2019
Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education, Hunan University of Science and Technology, Xiangtan, 411201, China.
Theoretical studies on the dimers formed by CO with the halides of multivalent astatine as a Lewis-acid center are carried out to examine the typical characteristics of supervalent halogen bonds. Calculations at the MP2/aug-cc-pVTZ level reveal that the multiple nucleophilic sites of multivalent halide monomers can promote the formation of various types of halogen bonds, among which the most stable ones are At-halogen bond complexes with multivalent astatine as a Lewis acid center, followed by the π-halogen bond dimers, and the weakest ones are the X-halogen bonds. Compared with multivalent Cl-, Br-, and I-centers, At, as the heaviest halogen, exhibits the highest halogen-bond donating ability.
View Article and Find Full Text PDFActa Crystallogr C Struct Chem
January 2017
Chemistry, Missouri State University, 901 South National Avenue, Springfield, MO 65897, USA.
Halogen bonding is a well-established and intensively studied intermolecular interaction that has also been used in the preparation of functional materials. While polyfluoroiodo- and polyfluorobromobenzenes have been widely used as aromatic halogen-bond donors, there have been very few studies of iodoimidazoles with regard to halogen bonding. We describe here the X-ray structures of three iodoimidazole derivatives, namely 1-benzyl-2-iodo-1H-imidazole, CHIN, (1), 1-benzyl-4-iodo-1H-imidazole, CHIN, (2), and 1-benzyl-2-iodo-1H-benzimidazole, CHIN, (3), and the halogen bonds that dominate the intermolecular interactions in each of these three structures.
View Article and Find Full Text PDFInorg Chem
July 2016
Department of Chemistry, The George Washington University, 800 22nd Street, Northwest, Washington, D.C. 20052, United States.
The syntheses and crystal structures of 16 new rare-earth (RE = La(3+)-Y(3+))-3,5-dichlorobenzoic acid-terpyridine molecular materials characterized via single-crystal and powder X-ray diffraction are reported. These 16 complexes consist of four unique structure types ranging from molecular dimers (La(3+) and Ce(3+)) to tetramers (Pr(3+)-Y(3+)) as one moves across the RE(3+) series. This structural evolution is accompanied by subsequent changes in modes of supramolecular assembly (halogen bonding, halogen-π, halogen-halogen, and π-π interactions).
View Article and Find Full Text PDFOrg Biomol Chem
January 2004
School of Chemical Sciences, The University of New South Wales, UNSW Sydney NSW 2052, Australia.
The preparation of 1,4,8,11-tetrabromo-5b[small alpha],6,12b[small alpha],13-tetrahydropentaleno[1,2-b:4,5-b[prime or minute]]diquinoline is described. This is a further member of the tetrahalo aryl host family, and forms crystalline lattice inclusion compounds with many guests. The X-ray structures of the allyl cyanide, 1,2,3-trichloropropane, chlorobenzene, toluene, benzene-water, methyl chloroform and carbon tetrachloride inclusion compounds are described, and compared with that of the solvent-free apohost.
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