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Advanced Organic Chemistry: Carbon-13 NMR spectrum of methyl 2-hydroxybenzoate

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Interpreting the Carbon-13 13C NMR spectrum of methyl 2-hydroxybenzoate

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 methyl 2-hydroxybenzoate (methyl salicylate)

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C-13 NMR spectroscopy - spectra index

13C nmr spectrum of methyl 2-hydroxybenzoate C8H8O3 analysis of chemical shifts ppm interpretation of C-13 chemical shifts ppm of methyl salicylate C13 carbon-13 nmr oil of wintergreen 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 - methyl 2-hydroxybenzoate here.

C8H8O3, (c) doc b or , methyl 2-hydroxybenzoate (methyl salicylate, 'oil of wintergreen'

For more see The molecular structure and naming of carboxylic acids and derivatives

For more see The molecular structure and naming of aromatic compounds

Interpreting the C-13 NMR spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

As you can see from the diagram above there are 8 different chemical shift lines in the C-13 NMR spectrum of methyl 2-hydroxybenzoate indicating 8 different chemical environments of the 8 carbon atoms of methyl 2-hydroxybenzoate.

13C chemical shifts δ (a) to (h) on the C-13 NMR spectrum diagram for methyl 2-hydroxybenzoate (methyl salicylate).

(a) gives the smallest 13C NMR chemical shift δ where the carbon atom is neither attached to, or part of, the benzene ring - though being attached to an electronegative oxygen atom increases it.

(b) gives the largest 13C NMR chemical shift δ where the carbon atom is attached to two electronegative oxygen atoms.

(c), (e)  and (g) give similar 13C NMR chemical shifts δ for carbon atoms 1, 3 and 5 of the benzene ring (clockwise numbering for minimum substituent numbers)

(d) gives a relatively large 13C NMR chemical shift δ where the carbon atom is linked to an oxygen atom.

(f) and (h) give similar 13C NMR chemical shifts δ for carbon atoms 4 and 6 of the benzene ring (larger than c, e and g).

The carbon-13 NMR spectra provides direct evidence of 8 different carbon atom environments for the 8 carbon atoms in the methyl 2-hydroxybenzoate molecule, deduced from the presence of 8 different 13C NMR chemical shifts (ppm).


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Links associated with methyl 2-hydroxybenzoate

The infrared spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

The mass spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

The H-1 NMR spectrum of methyl 2-hydroxybenzoate (methyl salicylate)

INDEX of all revision notes on CARBOXYLIC ACIDS and DERIVATIVES

INDEX of all AROMATIC COMPOUND chemistry revision notes

C-13 NMR spectroscopy index

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