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Carbon-13 NMR Spec.

Carbon-13 NMR spectrometry in organic analysis

13C NMR, is a valuable analytical technique used to study the carbon nuclei in organic compounds. It provides insights into the types of carbon atoms present in a molecule and their chemical environments. Here’s a concise account of carbon-13 NMR spectroscopy using ethanol as an example:

  1. Sample Preparation: To perform a carbon-13 NMR analysis of ethanol (C2H5OH), a small amount of pure ethanol is typically dissolved in a deuterated solvent like deuterated chloroform (CDCl3) or deuterated dimethyl sulfoxide (CD3SOCD3). 

  2. Instrumentation: Carbon-13 NMR spectroscopy requires a specialised NMR spectrometer equipped with a carbon-13 nucleus detection system. This instrument applies a strong magnetic field and radiofrequency (RF) pulses to the sample.

  3. Chemical Shift: In the carbon-13 NMR spectrum, the vertical axis represents signal intensity, and the horizontal axis represents chemical shift (δ) in parts per million (ppm). The chemical shift values for carbon nuclei depend on their chemical environment. In ethanol, there are two types of carbon atoms: those in the methyl (CH3) group and those in the methylene (CH2) group.

  4. Spectral Information: The carbon-13 NMR spectrum of ethanol would typically show two distinct peaks corresponding to the two types of carbon atoms present. The chemical shift values for these peaks provide information about the carbon environments. The peak corresponding to the CH3 group will appear at a different chemical shift compared to the peak corresponding to the CH2 group.

  5. Peak Multiplicity: Unlike proton NMR, carbon-13 NMR spectra do not typically exhibit splitting patterns (multiplicity).

  6. Integration: Integration of the peaks in a carbon-13 NMR spectrum provides information about the relative number of carbon atoms in each environment.
    Just as with proton nmr, the ratio of the areas under the peaks
    ≡ ratio of carbons in the different environments.

  7. Peak Assignment: Experienced chemists can assign the peaks in the spectrum to specific carbon atoms in the molecule by analysing chemical shifts and integration values.

In summary, carbon-13 NMR spectroscopy is a valuable tool for analysing the carbon nuclei in organic molecules like ethanol. It provides information about chemical shifts, integration, and the types of carbon atoms present in the compound. This technique is essential for structural elucidation and chemical characterization in chemistry and related fields.

THE CAUSE OF CHEMICAL SHIFTS:

  1. PROXIMITY TO AN ELECTRONEGATIVE ATOM (e.g N,O,F and Cl)
  2. PROXIMITY TO PI BONDS (sideways-overlapping p atomic orbitals)

Carbon-13

What is the percentage of
13C isotopes in nature?

1%

The spectromter therefore needs to be more sensitive than for proton nmr, and spectra take longer to record.

Reference Agent

What do you understand by this term?

Tetramethylsilane

It is TMS  & the chemical environments of 13C atoms in a molecule are compared with that of the 13C atom in TMS.

   NMR tube.
   The sample is prepared in a     thin-walled glass tube.

Reference Agent

3 reasons for using this particular reference agent.

1. Carbon is more electronegative than silicon and hydrogen.

This means that it is more shielded in this molecule than in the majority of organic molecules

The TMS peak will therefore not overlap with the peaks for the carbon atoms in the analyte.

2. Non-toxic

3. Volatile, making it easy to recover the sample.

Look for symmetry.

  1-bromopropane does not have symmetry,
while 2 bromopropane does.

Number of carbon enviroments in

CH3CH2CHBrCH2CH3

Three

Number of carbon enviroments in

pentan-2-one CH3COCH2CH2CH3

Five

Number of carbon enviroments in

pentan-3-one CH3CH2COCH2CH3

Three

Number of carbon enviroments in

cyclohexane C6H12

One

Number of carbon enviroments in

cyclohexene C6H10

Three

Number of carbon enviroments in

2,4-dinitrochlorobenzene

Four

Number of carbon enviroments in

1,3-dibromo-2,2-dimethylpropane

Three

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