Related Experiment Video
Updated: Jul 14, 2026
10:42
Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)
Published on: December 29, 2016
Solid state structure and solution behaviour of organoselenium(II) compounds containing 2-{E(CH2CH2)2NCH2}C6H4 groups
Monika Kulcsar1, Anca Beleaga, Cristian Silvestru
1Faculty of Chemistry and Chemical Engineering, "Babes-Bolyai" University, RO-400028, Cluj-Napoca, Romania.
Dalton Transactions (Cambridge, England : 2003)
|May 22, 2007
Summary
This study details the cleavage of selenium-selenium bonds in specific organoselenium compounds using halogenating agents. The resulting compounds exhibit unique T-shaped coordination geometries, confirmed by X-ray diffraction and NMR spectroscopy.
Area of Science:
- Organometallic Chemistry
- Inorganic Chemistry
- Crystallography
Background:
- Disulfide bond cleavage is crucial in various chemical and biological processes.
- Organoselenium compounds offer unique reactivity and structural properties.
- Understanding the coordination chemistry of selenium is vital for developing new materials and catalysts.
Purpose of the Study:
- To investigate the cleavage of the selenium-selenium (Se-Se) bond in novel organoselenium compounds.
- To characterize the resulting organoselenium halide compounds using spectroscopic and crystallographic methods.
- To elucidate the coordination geometry and supramolecular interactions in these compounds.
Main Methods:
- Synthesis of organoselenium compounds [2-{O(CH2)CH2)2NCH2}C6H4]2Se2 (1) and [2-{MeN(CH2)CH2)2NCH2}C6H4]2Se2 (2).
- Cleavage of the Se-Se bond using sulfuryl chloride (SO2Cl2), bromine (Br2), or iodine (I2).
- Characterization by Nuclear Magnetic Resonance (NMR) spectroscopy (1H, 13C, 15N, 77Se, 2D NMR) and single crystal X-ray diffraction.
Main Results:
- Successful cleavage of the Se-Se bond in compounds 1 and 2, yielding organoselenium halide compounds [2-{O(CH2)CH2)2NCH2}C6H4]SeX (3-5) and [2-{MeN(CH2)CH2)2NCH2}C6H4]SeI (6).
- Determination of T-shaped coordination geometries for all synthesized and characterized compounds.
- Identification of supramolecular associations in the crystal structures driven by hydrogen bonding.
Conclusions:
- The Se-Se bond in the studied organoselenium compounds is readily cleaved by common halogenating agents.
- The resulting organoselenium halides adopt characteristic T-shaped coordination geometries.
- Crystal structures reveal significant supramolecular organization through hydrogen bonding.
Related Concept Videos
01:23Properties of Organometallic Compounds
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
02:34Structural Isomerism
Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
02:54Lewis Structures of Molecular Compounds and Polyatomic Ions
To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:
02:54Coordination Compounds and Nomenclature
In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
02:17Structure and Nomenclature of Thiols and Sulfides
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...
02:55Exceptions to the Octet Rule
Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories: