Related Experiment Video
Updated: May 26, 2026
08:51
Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
5,8-Dibromo-15-nitro-2,11-dithia-[3.3]paracyclo-phane
1Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|December 27, 2011
Summary
This study details the crystal structure of a novel dibromo-nitro-dithia compound. Weak intermolecular interactions and atomic disorder were key findings in its unique molecular arrangement.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the solid-state properties of complex organic molecules is crucial for designing new materials.
- The specific arrangement of atoms and intermolecular forces dictates a compound's physical and chemical behavior.
- Tricyclic organic compounds with heteroatoms offer unique structural motifs for investigation.
Purpose of the Study:
- To elucidate the crystal structure of 13,15-dibromo-6-nitro-3,10-dithia-tricyclo-[10.2.2.2(5,8)]octa-deca-1(14),5,7,12,15,17-hexa-ene.
- To analyze the intermolecular interactions and structural features influencing crystal packing.
- To identify and characterize any atomic disorder within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
- Intermolecular interactions, such as π-π stacking, were quantified using centroid-centroid distances.
- Disorder in atomic positions was modeled and refined.
Main Results:
- The dihedral angle between the two benzene rings in the title compound was determined to be 0.93(2)°.
- Weak π-π intermolecular interactions, with a centroid-centroid distance of 3.286(5) Å, stabilize the crystal structure.
- Significant disorder was observed for one sulfur atom (occupancy 0.91:0.09) and associated hydrogen atoms (occupancy 0.93:0.07).
Conclusions:
- The crystal structure of the title compound is characterized by a near-planar arrangement of its benzene rings and stabilized by π-π stacking.
- Atomic disorder in sulfur and hydrogen atoms is a notable feature of this crystal structure.
- These findings contribute to the understanding of structure-property relationships in complex heterocyclic organic compounds.
Related Concept Videos
02:46Halogenation of Alkenes
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
01:13Five-Membered Heterocyclic Aromatic Compounds: Overview
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
01:14Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
02:30Chirality at Nitrogen, Phosphorus, and Sulfur
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
02:39Nomenclature of Alkynes
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes: