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Related Concept Videos

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

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Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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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...
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Chirality02:25

Chirality

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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Chirality in Nature02:30

Chirality in Nature

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Prochirality02:05

Prochirality

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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...
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A Computational Study of Chalcogen-containing H<sub>2</sub> X…YF and (CH<sub>3</sub> )<sub>2</sub> X…YF (X=O, S, Se; Y=F, Cl, H) and Pnicogen-containing H<sub>3</sub> X'…YF and (CH<sub>3</sub> )<sub>3</sub> X'…YF (X'=N, P, As) Complexes.

Chemphyschem : a European journal of chemical physics and physical chemistry·2018
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Communication: permanent dipoles contribute to electric polarization in chiral NMR spectra.

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Cooperative effects in FH/Li⋯HCCX⋯OH2 complexes (X=F, Cl, Br, H).

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy·2013
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Cooperative hydrogen bonding in trimers involving HCN and HBO.

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Cooperative and diminutive hydrogen bonding in Y...HCN...HCN and NCH...Y...HCN trimers (Y=BF,CO,N2).

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Chiral discrimination in NMR spectroscopy.

A David Buckingham1

  • 1Department of Chemistry,Cambridge University,Cambridge CB2 1EW,UK.

Quarterly Reviews of Biophysics
|November 6, 2015
PubMed
Summary

Nuclear magnetic resonance (NMR) can now detect molecular chirality. Precessing nuclear spins in chiral molecules generate a detectable electric polarization, enabling enantiomer differentiation.

Area of Science:

  • Chemistry
  • Biochemistry
  • Spectroscopy

Background:

  • Nuclear magnetic resonance (NMR) is a vital tool in chemistry and biochemistry.
  • Traditional NMR spectroscopy is insensitive to molecular chirality.
  • Chirality is crucial in biological systems and drug development.

Purpose of the Study:

  • To explore the theoretical prediction of chirally sensitive NMR signals.
  • To assess the progress in experimentally realizing chiral discrimination using NMR.
  • To investigate methods for detecting enantiomers via NMR.

Main Methods:

  • Theoretical analysis of nuclear spin dynamics in chiral molecules under strong magnetic fields.
  • Investigation of induced electric polarization and its relation to molecular chirality.
Keywords:
Chiral discrimination NMR spectroscopy Pseudoscalar molecular properties

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  • Exploration of the role of molecular dipole moments and shielding tensors.
  • Consideration of electric field-induced magnetization as an alternative detection method.

    • Main Results:

    • Nuclear spins in chiral molecules, under specific conditions, can induce a detectable electric polarization.
    • This polarization exhibits opposite signs for enantiomers, providing a basis for chiral discrimination.
    • The effect is enhanced in dipolar molecules due to partial orientation.
    • An applied electric field can induce chirally sensitive magnetization.

    Conclusions:

    • NMR spectroscopy has theoretical potential for detecting molecular chirality.
    • Experimental realization of chirally sensitive NMR is progressing.
    • These advancements could revolutionize enantiomeric analysis in chemistry and biochemistry.