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Advanced Organic Chemistry: Carbon-13 NMR spectrum of propanamide

The Carbon-13 NMR spectrum of propanamide (propionamide)

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 propanamide

C-13 nmr spectrum of propanamide analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of propionamide 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 shifts, called chemical shifts, depend on the individual (electronic) chemical environment of the 13C atoms in an organic molecule - propanamide here.

propanamide (propionamide), C3H7NO, (c) doc b, (c) doc b, (c) doc b

Interpreting the C-13 NMR spectrum of Propanamide

As you can see from the diagram above there are 3 different chemical shift lines in the C-13 NMR spectrum of propanamide indicating 3 different chemical environments of the carbon atoms.

CH3CH2CONH2

Note the 3 colours indicating the 3 different chemical environment of the carbon atoms in propanamide.

Note the decreasing effect on the chemical shift as the carbon atom is further from the highly electronegative oxygen and nitrogen atoms of propanamide.

The carbon-13 NMR spectra a provides direct evidence of 3 different carbon atom environments in the propanamide molecule from 3 different chemical shifts (ppm).


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