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¹H NMR of Labile Protons: Deuterium (²H) Substitution

¹H NMR of Labile Protons: Deuterium (²H) Substitution

This lesson illustrates the role of deuterium substitution in simplifying the NMR spectrum of compounds comprising labile protons. One method employed is the use of deuterium. Amongst the three isotopes of hydrogen, deuterium (2H) has a nucleus composed of one proton and one neutron. When the D2O solvent is added to a pure dry ethanol solution, its labile proton is substituted with deuterium.

Molecular Orbital Theory II

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π Molecular Orbitals of 1,3-Butadiene

π 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...

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sp3d and sp3d 2 Hybridization

π Electron Effects on Chemical Shift: Overview

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An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0, resulting in...

Stability of Conjugated Dienes

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

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Related Experiment Video

Updated: May 19, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Published on: July 19, 2019

Do deuteriums form stronger CH-π interactions?

Chen Zhao¹, Robert M Parrish, Mark D Smith

¹Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA.

Journal of the American Chemical Society

|August 21, 2012

Summary

This summary is machine-generated.

The D/H isotope effect on CH-π interactions was investigated. Both experimental and computational studies found no significant difference, suggesting this isotope effect is minimal or absent for CH-π interactions.

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Neutron Crystallography Data Collection and Processing for Modelling Hydrogen Atoms in Protein Structures

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Last Updated: May 19, 2026

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Neutron Crystallography Data Collection and Processing for Modelling Hydrogen Atoms in Protein Structures

Neutron Crystallography Data Collection and Processing for Modelling Hydrogen Atoms in Protein Structures

Published on: December 1, 2020

Area of Science:

Supramolecular Chemistry
Isotope Effects
Computational Chemistry

Background:

CH-π interactions are crucial non-covalent forces in molecular recognition and self-assembly.
Understanding the influence of isotopic substitution on these interactions is important for molecular design.

Purpose of the Study:

To experimentally and computationally investigate the D/H isotope effect on the strength of CH-π interactions.
To determine if deuteration of the CH group significantly alters CH-π interaction strength.

Main Methods:

Synthesis of molecular balances with deuterated (CD-π) and non-deuterated (CH-π) alkyl groups.
X-ray crystallography to characterize solid-state geometries.
Nuclear Magnetic Resonance (NMR) spectroscopy to quantify interaction strength in solution.
Density Functional Theory (DFT) calculations to assess interaction energies.

Main Results:

Experimental and computational studies showed no significant difference between CH-π and CD-π interactions.
The folded/unfolded ratios measured by NMR were comparable for both deuterated and non-deuterated compounds.
DFT calculations corroborated the experimental findings, indicating a negligible isotope effect.

Conclusions:

The D/H isotope effect for CH-π interactions is very small or nonexistent.
Isotopic substitution with deuterium does not substantially impact the strength of CH-π interactions.