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Related Concept Videos

2D NMR: Overview of Heteronuclear Correlation Techniques01:18

2D NMR: Overview of Heteronuclear Correlation Techniques

Heteronuclear correlation spectroscopy is an analytical technique that investigates the coupling between different types of nuclei, often a proton and an X-nucleus, such as carbon-13 or nitrogen-15. This method is commonly used in nuclear magnetic resonance (NMR) spectroscopy to gain insights into complex chemical compounds' structural and compositional aspects. A typical heteronuclear correlation spectrum displays X-nucleus chemical shifts on one axis and a proton spectrum on the other axis.
2D NMR: Overview of Homonuclear Correlation Techniques01:16

2D NMR: Overview of Homonuclear Correlation Techniques

Homonuclear correlation spectroscopy (COSY) is a powerful technique used in Nuclear Magnetic Resonance (NMR) spectroscopy to study the correlations between nuclei of the same type within a molecule. It provides information about scalar couplings between adjacent nuclei, which helps determine connectivity and structural information. There are several COSY variants, each with its unique strengths and experimental parameters.
COSY90 is the standard two-dimensional (2D) COSY experiment that...
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene π orbitals.
2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)01:19

2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)

Heteronuclear single-quantum correlation spectroscopy (HSQC) is a 2D NMR technique that reveals one-bond correlations between hydrogen and a heteronucleus. The HSQC experiment is similar to the heteronuclear correlation experiment (HETCOR) but is more sensitive. In the HSQC spectrum, the proton chemical shift is plotted on the horizontal F2 axis, while the 13C chemical shift is plotted on the vertical F1 axis. The corresponding proton and 13C spectra are also shown. The HSQC contour plot does...
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
Spin–Spin Coupling Constant: Overview01:08

Spin–Spin Coupling Constant: Overview

In bromoethane, the three methyl protons are coupled to the two methylene protons that are three bonds away. In accordance with the n+1 rule, the signal from the methyl protons is split into three peaks with 1:2:1 relative intensities. The methylene protons appear as a quartet, with the relative intensities of 1:3:3:1.
Qualitatively, any spin plus-half nucleus polarizes the spins of its electrons to the minus-half state. Consequently, the paired electron in the hydrogen–carbon bond must have a...

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An efficient stereochemical elucidation of the aromatic polyketide NFAT-133 using the novel NOE quantification combined with <i><sup>n</sup>J</i> <sub>H-H</sub> and <i><sup>n</sup>J</i> <sub>C-H</sub> coupling constants.

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Single-Molecule F&ouml;rster Resonance Energy Transfer Methods for Real-Time Investigation of the Holliday Junction Resolution by GEN1
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Single-Molecule Förster Resonance Energy Transfer Methods for Real-Time Investigation of the Holliday Junction Resolution by GEN1

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Selective J-resolved HMBC, an efficient method for measuring heteronuclear long-range coupling constants.

Kazuo Furihata1, Mitsuru Tashiro, Haruo Seto

  • 1Division of Agriculture and Agricultural Life Sciences, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. furihata@iam.u-tokyo.ac.jp

Magnetic Resonance in Chemistry : MRC
|August 12, 2009
PubMed
Summary

A new selective J-resolved heteronuclear multiple-bond correlation (HMBC) pulse sequence efficiently measures long-range carbon-hydrogen coupling constants (J(C-H)). This method simplifies analysis and enhances sensitivity for complex molecules.

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Area of Science:

  • Nuclear Magnetic Resonance (NMR) Spectroscopy
  • Organic Chemistry
  • Analytical Chemistry

Background:

  • Measuring long-range carbon-hydrogen coupling constants (J(C-H)) is crucial for structural elucidation of organic molecules.
  • Existing Heteronuclear Multiple-Bond Correlation (HMBC) based methods often suffer from complex spectra and lower sensitivity, hindering accurate analysis.
  • Previous J-resolved HMBC methods provided improvements but still had limitations.

Purpose of the Study:

  • To develop a novel and efficient pulse sequence for accurate measurement of long-range J(C-H) coupling constants.
  • To overcome the limitations of existing HMBC-based pulse sequences, particularly in terms of spectral simplicity and sensitivity.
  • To provide a robust tool for the structural analysis of complex natural products.

Main Methods:

  • Development of a selective J-resolved HMBC pulse sequence.
  • Modification of the standard HMBC scheme by incorporating a selective (1)H 180-degree pulse.
  • Utilizing a constant-time (CT) HMBC approach within the J-resolved framework.
  • Application of the novel sequence to the analysis of complex natural products, portmicin and monazomycin.

Main Results:

  • The developed selective J-resolved HMBC sequence yields only long-range J(C-H) cross peaks, simplifying spectral interpretation.
  • The new method demonstrates high sensitivity, comparable to or better than previous techniques.
  • Accurate measurement of long-range J(C-H) coupling constants was achieved for complex molecules.
  • The sequence effectively overcomes disadvantages associated with earlier HMBC-based methods.

Conclusions:

  • The selective J-resolved HMBC pulse sequence is an efficient and accurate method for measuring long-range J(C-H) coupling constants.
  • This technique offers significant advantages in spectral simplicity and sensitivity, facilitating the structural elucidation of complex organic compounds.
  • The successful application to portmicin and monazomycin validates its utility in natural product chemistry.