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Related Concept Videos

Isomerism02:43

Isomerism

21.8K
Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Stereoisomers02:32

Stereoisomers

16.5K
On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
16.5K
Stereoisomerism02:52

Stereoisomerism

12.8K
Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
12.8K
Isomerism in Alkenes02:01

Isomerism in Alkenes

13.7K
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...
13.7K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

14.1K
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
14.1K

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Stereoisomerization during Molecular Packing.

Shidang Xu1, Yukun Duan1, Purnima Manghnani1

  • 1Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore, 117585, Singapore.

Advanced Materials (Deerfield Beach, Fla.)
|April 29, 2021
PubMed
Summary
This summary is machine-generated.

Researchers discovered a new type of isomerization that occurs during molecular packing, not requiring external energy. This process, observed in donor-acceptor-donor molecules, leads to highly efficient organic solids.

Keywords:
molecular designmolecular packingsolid-state materialsstereoisomerization

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Area of Science:

  • Organic Chemistry
  • Solid-State Chemistry
  • Crystallography

Background:

  • Isomerization traditionally requires external energy inputs like light or heat.
  • Molecular packing is a critical factor influencing material properties in the solid state.

Purpose of the Study:

  • To describe a novel isomerization phenomenon occurring spontaneously during molecular packing.
  • To demonstrate this isomerization in symmetric donor-acceptor-donor (D-A-D) molecules.
  • To investigate the resulting properties of the solid-state materials.

Main Methods:

  • Synthesis and characterization of symmetric D-A-D molecules with stereoisomeric donor units.
  • Crystallographic analysis to identify and confirm the presence of asymmetric isomers in the solid state.
  • Spectroscopic and photophysical measurements to evaluate the efficiency of the resulting organic solids.

Main Results:

  • Demonstrated a new form of isomerization that occurs solely during the molecular packing process.
  • Confirmed the formation of asymmetric isomers within crystal structures of D-A-D molecules.
  • Observed highly efficient organic solids with quantum yields approaching unity due to restricted intramolecular motion in the asymmetric solid-state geometry.

Conclusions:

  • Molecular packing can induce isomerization without external energy, offering a new pathway for material design.
  • The asymmetric geometry formed during packing is key to achieving high photophysical efficiency in organic solids.
  • This discovery opens avenues for developing novel organic materials with tailored properties through controlled crystallization.