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Advanced Organic Chemistry: Carbon-13 NMR spectrum of cyclobutane

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Interpreting the Carbon-13 NMR spectrum of cyclobutane

Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK IB KS5 A/AS GCE advanced A level organic chemistry students US K12 grade 11 grade 12 organic chemistry courses involving molecular spectroscopy analysing C-13 NMR spectra of cyclobutane

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C-13 NMR spectroscopy - spectra index

13C nmr spectrum of cyclobutane C4H8 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of cyclobutane C13 13-C nmr doc brown's advanced organic chemistry revision notes 

TMS is the acronym for tetramethylsilane, formula Si(CH3)4, whose 13C atoms are arbitrarily given a chemical shift of 0.0 ppm. This is the 'standard' in 13C NMR spectroscopy and all other 13C resonances, called chemical shifts, are measured with respect to the TMS, and depend on the individual (electronic) chemical environment of the 13C atoms in an organic molecule - cyclobutane here.

Cyclobutane, C4H8 , alkanes structure and naming (c) doc b, alkanes structure and naming (c) doc b

Interpreting the C-13 NMR spectrum of cyclobutane

As you can see from the diagram above there is only one chemical shift line in the C-13 NMR spectrum of cyclobutane indicating just one chemical environments of the 4 carbon atoms of cyclobutane.

13C chemical shift (a) 22.4 ppm on the C-13 NMR spectrum diagram for cyclobutane.

The carbon-13 NMR spectra provides direct evidence of only one carbon atom environment for the 4 carbon atoms in the cyclobutane molecule, deduced from the presence of just one 13C NMR chemical shift of 22.4 ppm.

Cyclobutane is NOT a true planar molecular arrangement in terms of the four carbon atoms because the square is slightly folded.

However all 4 hydrogen atoms of cyclobutane appear to be in the same chemical environment and give the same chemical shift i.e. there are 4 equivalent carbon atoms in the cyclobutane molecule and just one single 13C NMR resonance signal.

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Links associated with cyclobutane

The chemistry of ALKANES revision notes INDEX

The infrared spectrum of cyclobutane

The mass spectrum of cyclobutane

The H-1 NMR spectrum of cyclobutane

C-13 NMR spectroscopy index


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