Related Experiment Video
Updated: Jun 1, 2026
12:56
Seeded Synthesis of CdSe/CdS Rod and Tetrapod Nanocrystals
Published on: December 11, 2013
2-Isobutyl-2-phosphabicyclo-[3.3.1]nonane 2-selenide.
Summary
This study introduces the first phosphine structure featuring the bicyclic 2-phospha-bicyclo-[3.3.1]nonane unit. The compound crystallizes as a racemic mixture, with determined P-Se bond distances and steric parameters like the Tolman cone angle.
Area of Science:
- Organometallic Chemistry
- Crystallography
- Stereochemistry
Background:
- Phosphine ligands are crucial in catalysis and materials science.
- The bicyclic 2-phospha-bicyclo-[3.3.1]nonane (VCH) unit offers unique structural and electronic properties.
- Exploring novel phosphine structures expands the toolkit for chemical synthesis.
Purpose of the Study:
- To synthesize and characterize the first phosphine compound incorporating the VCH unit.
- To determine the structural and stereochemical features of this novel phosphine.
- To evaluate its steric properties using established parameters.
Main Methods:
- Single-crystal X-ray diffraction was employed for structural determination.
- The compound's stereochemistry was analyzed, identifying chiral centers.
- Tolman cone angles were calculated to assess steric bulk.
Main Results:
- The title compound, C(12)H(23)PSe, was successfully synthesized and structurally elucidated.
- It contains two chiral centers, existing as a racemic mixture of R,R- and S,S-enantiomers.
- A typical P-Se bond distance of 2.1360(16) Å was observed.
- Calculated Tolman cone angle is 163°, with an effective cone angle of 168°.
Conclusions:
- This work presents the first crystallographic data for a phosphine bearing the VCH moiety.
- The compound exhibits racemic stereochemistry and significant steric bulk, as indicated by its cone angles.
- This novel phosphine structure provides a new building block for organophosphorus chemistry and catalysis.
More Related Videos
08:15Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups
Published on: February 11, 2012
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Related Concept Videos
02:26Preparation and Reactions of Sulfides
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
01:24π Molecular Orbitals of 1,3-Butadiene
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
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.
02:05Prochirality
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
02:01Isomerism in Alkenes
Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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...