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Related Concept Videos

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
Induced Electric Dipoles01:28

Induced Electric Dipoles

A permanent electric dipole orients itself along an external electric field. This rotation can be quantified by defining the potential energy because the external torque does work in rotating it. Then, the potential energy is minimum at the parallel configuration and maximum at the antiparallel configuration. While the former is a stable equilibrium, the latter is an unstable equilibrium.
Since the absolute value of potential energy holds no physical meaning, its zero value can be chosen as per...
Stereoisomerism02:52

Stereoisomerism

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...
IR Spectrum Peak Splitting: Symmetric vs Asymmetric Vibrations01:08

IR Spectrum Peak Splitting: Symmetric vs Asymmetric Vibrations

Identical bonds within a polyatomic group can stretch symmetrically (in-phase) or asymmetrically (out-of-phase). Similar to hydrogen bonding, these vibrations also influence the shape of the IR peak. Generally, asymmetric stretching frequencies are higher than symmetric stretching frequencies. For example, primary amines exhibit two distinct IR peaks between 3300–3500 cm−1 corresponding to the symmetric and asymmetric N-H stretching, while secondary amines exhibit a single stretching vibration...
Inductive Effects on Chemical Shift: Overview01:27

Inductive Effects on Chemical Shift: Overview

The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...
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Stereoisomers

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 restricted...

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Stereoinduction by distortional asymmetry.

Robert V Kolakowski1, Lawrence J Williams

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, NJ 08903, USA.

Nature Chemistry
|December 3, 2010
PubMed
Summary

A new distortional asymmetry model explains stereoselective synthesis in cyclic systems. This model accounts for face selectivity where other theories fail, improving understanding of chemical reactions.

Area of Science:

  • Organic Chemistry
  • Chemical Synthesis
  • Stereochemistry

Background:

  • Stereoselective synthesis demands differentiation between the two faces of a π bond.
  • Existing qualitative models for stereoinduction often fail in sterically unbiased cyclic systems.

Purpose of the Study:

  • To introduce the distortional asymmetry model for understanding face selectivity in chemical synthesis.
  • To explain stereoinduction in cyclic systems where traditional models are inadequate.

Main Methods:

  • Computational analysis including out-of-plane distortional potential calculations and transition state calculations.
  • Molecular orbital analysis.
  • Comparison of theoretical predictions with experimental data.

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Main Results:

  • The distortional asymmetry model identifies conditions where ground state contributions significantly influence face selectivity.
  • Computational and experimental data align, supporting the model's validity.
  • The model explains experimental observations not attributable to steric, torsion, polar, or emergent transition state effects.

Conclusions:

  • The distortional asymmetry model provides novel insight into stereoselective chemical synthesis.
  • The model offers a readily understandable framework based on reaction theory.
  • It enhances the explanatory power for complex stereochemical outcomes in cyclic systems.