Advanced Organic Chemistry: Infrared spectrum of d-glucose C6H12O6

Interpreting and explaining the infrared spectrum of d-glucose

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 Infrared spectroscopy - spectra index

Introductory note on the infrared spectrum of glucose

Students and teachers please note my explanation of the infrared spectrum of glucose is designed for advanced, but pre-university, chemistry courses.

Based in the infrared spectrum diagram for glucose, only some of the most prominent peaks for particular bond vibrations are discussed, particularly if glucose has a functional group with a particular characteristic wavenumber peak.

The infrared spectrum of glucose is unique and the whole, or selected wavenumbers, can be used to fingerprint its identity, sometimes analysing a mixture containing glucose or following its change of concentration in a reaction.

infrared spectrum of d-glucose C6H12O6 wavenumbers cm-1 functional group detection fingerprint pattern identification of d-glucose doc brown's advanced organic chemistry revision notes  

molecular structure of glucose structural formula of d-glucose molecular formular C6H12O6Spectra obtained from a nujol mull of d-glucose, so thee is an overlap of two spectra.

The right-hand part of the of the infrared spectrum of d-glucose, wavenumbers ~1500 to 400 cm-1 is considered the fingerprint region for the identification of d-glucose and most organic compounds.

It is due to a unique set of complex overlapping vibrations of the atoms of the molecule of d-glucose.

d-glucose, C6H12O6 has several functional groups - one C-O-C ether linkage, one primary alcohol group and four secondary alcohol groups.

d-glucose equilibrium formed between alpha α-D-glucopyranose and beta β-D-glucopyranose molecular structures

The d-glucose equilibrium formed between α-D-glucopyranose and β-D-glucopyranose

Interpretation of the infrared spectrum of d-glucose

The most prominent infrared absorption lines of d-glucose (wavenumber bands in cm-1)

From ~3700 to ~2500 cm-1 there two broad overlapping bands from O-H and C-H stretching vibrations.

The bands are complicated by hydrogen bonding affecting the O-H vibration frequencies and the O-H vibrations can originate from both primary and secondary alcohol groups.

Absorptions in the 3500 to 3200 cm-1 region are mainly due to the O-H stretching vibrations and the twin peaks may originate from the primary alcohol group as well as the secondary alcohol groups.

Absorptions in the 3000 to 2800 cm-1 region are mainly due to the C-H stretching vibrations.

C-O stretching vibrations for the C-O C ether group occur at ~1140 to 1070 cm-1.

C-O vibrations from a primary alcohol group usually occur at ~1075 to 1000 cm-1.

C-O vibrations from a secondary alcohol group occur at ~1150 to 1075 cm-1.

The absence of other specific functional group bands will show that a particular functional group is absent from the d-glucose molecular structure.

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