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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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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

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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...
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Naming Enantiomers02:21

Naming Enantiomers

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three...
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Isomerism02:43

Isomerism

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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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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Transition between [R]- and [S]-stereoisomers without bond breaking.

Shampa Raghunathan1, Komal Yadav2, V C Rojisha1

  • 1Center for Computational Natural Sciences and Bioinformatics International Institute of Information Technology, Hyderabad 500 032, India. deva@iiit.ac.in.

Physical Chemistry Chemical Physics : PCCP
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Summary
This summary is machine-generated.

Researchers demonstrate molecular systems that undergo stereochemical inversion at tetrahedral centers via planar transition states or intermediates. This finding addresses a fifty-year-old chemical proposal for nondissociative racemization reactions.

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Area of Science:

  • Stereochemistry
  • Computational Chemistry
  • Reaction Mechanisms

Background:

  • A fifty-year-old proposal by Hoffmann suggested nondissociative racemization of tetrahedral centers via planar transition states.
  • Despite extensive research, no molecular system has been found to exhibit this specific racemization mechanism.

Purpose of the Study:

  • To investigate molecular species capable of undergoing stereochemical inversion at tetrahedral centers.
  • To explore the possibility of achieving racemization through planar transition states or intermediates.

Main Methods:

  • Quantum mechanical calculations
  • Ab initio quasi-classical dynamics simulations
  • Born-Oppenheimer molecular dynamics (BOMD)

Main Results:

  • Identified molecular species exhibiting stereochemical inversion around tetrahedral centers (Si, Al-, P+).
  • Demonstrated that this inversion can occur via either a planar transition state or a planar intermediate state.

Conclusions:

  • This study provides the first examples of molecular systems that can undergo stereochemical inversion via planar states, fulfilling a long-standing chemical proposal.
  • The findings are expected to guide future research into the fundamental phenomenon of nondissociative racemization.