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Advanced Organic Chemistry: Carbon-13 NMR spectrum of Methylbenzene

Carbon-13 NMR spectrum of Methylbenzene (Toluene)

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

C-13 nmr spectrum of methylbenzene analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of methylbenzene 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 shifts, called chemical shifts, depend on the individual (electronic) chemical environment of the 13C atoms in an organic molecule - methylbenzene Methylbenzene  C7H8, C6H5CH3 (c) doc b , (c) doc b , (c) doc b

Interpreting the C-13 NMR spectrum of Methylbenzene (Toluene)

As you can see from the diagram above there are only 5 chemical shift lines in the C-13 NMR spectrum of methylbenzene indicating 5 different chemical environments of carbon atoms.

Apart from the side-chain methyl group carbon atom 7, the ring carbons can occupy the 4 different positions on benzene ring of methylbenzene (carbon atoms 1, 2 = 6, 3 = 5 and 4 on the diagram above).

Therefore you see 5 chemical shift lines in the C-13 NMR spectrum of methylbenzene.

Apart from carbon atom 1 next to, and influenced by, the other ring carbon atoms show a similar chemical shift ~125 to 129 ppm, perhaps not surprising given the symmetry and electron distribution of the benzene ring.

The side-chain 'aliphatic' carbon atom of methylbenzene has very different chemical shift than the benzene ring carbon atoms.


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