CHEM 2203

Experiment 2- Infrared Spectrometry

Zhiqiao Xiao
101083582
Date performed: 11 May 2022
Lab partner: Haoyang Wang
Results and calculations
Table1. Experimental Peak and literature peak (cm-1) of functional groups include H-O, C=O, and
C=C of salicylic acid.
Functional Groups Experimental Peak (cm-1) Literature Peak(cm-1)
H-O, hydroxyl 3600-2400 3400-2500
C=O, carbonyl 1661.6 1662
C=C, aromatic 1613.4; 1484.2 1613; 1484

The table above summarize the values of experimental peak and literature peak of salicylic acid.
The literature peak value was from the Spectral Database for Organic Compounds (SDBS). The
functional groups include hydroxyl (H-O), carbonyl(C=O) as well as aromatic (C=C). For H-O,
the wavelength ranges from 3600-2400 cm-1 of the experiment and close to that of the literature
value, which range from 3400-2500 cm -1. For C=O, the experimental peak is appeared to be at
1661.6 cm-1 while the literature value is 1662 cm-1. Lastly, for C=C, the experimental peaks were
at 1613.4 and 1484.2 cm-1, while the literature peaks are 1613 and 1484 cm-1.

Figure1. Experimental IR spectrum of salicylic acid with KBr pellet, including the
structure, peaks and labelled functional group.
Figure2. Literature IR spectrum of salicylic acid with KBr pellet, including its Lewis
structure, peaks and labelled functional group.

Discussion
The purpose of this experiment is to obtain an infrared (IR) spectrometry of salicylic acid and
determine the purity of salicylic acid by compare the experimental IR spectrum to the literature
IR spectrum.

When a molecule irradiated with infrared light, the light is absorbed by the molecule under some
specific conditions. The energy of the absorbed infrared light is equal that of the energy
difference of a certain energy level of vibration of the molecule and another energy level of
vibration of that molecule1 (Ghosh, 2001). The application of Infrared (IR) spectroscopy is
conducive to determine the molecular composition of polymers by analyzing the characteristic
vibrations of their functional groups (Hsu, 1989). Thus, the infrared absorption spectrum is
vibrational spectrum of the molecule.

The peaks of the diagnostic (O-H) of the spectrum are broad, range from 3600-2400 cm -1, the
fingerprint region is different that of diagnostic region, with sharp peaks at 1661.6 cm -1, 1613.4
and 1484.2 cm-1, which indicate C=O carbonyl group and C=C aromatic group of salicylic acid.
Also, there are peaks that are obvious in the fingerprint region as well, such as at 1089.9 cm -1 and
at 758.87 cm-1. The main difference of the broad range and the sharp peaks is due to hydrogen
bonding of the O-H group of salicylic acid. The conjugation of carbonyl group shifts the IR
wavelength to a lower wavenumber. The electrons are based in the C=O group firmly, when
there is conjugation introduced, the electrons delocalize and thus weakens C=O bond and
moving the spectra to a lower wavenumber.

There are both medium/strong peaks and multiple sharp tips from 3300-2600 cm -1 of the
experimental IR and 3300-2500 cm-1 of the literature IR, which indicate the C-H group. At
1661.6 cm-1 of the experimental IR and 1662 cm-1 of literature IR there is a sharp peak, indicating
the C=O carbonyl group. In experimental IR, there are peaks range from 3234.7 to 2400 cm -1,
and the peaks range from 3240 to 2500 of the literature one, both demonstrate the O-H from
acid. The O-H phenol of experimental IR ranges from 3600-3300 cm -1 while for literature range
from 3500-3200 cm-1.

The fingerprint areas are similar between the experimental IR and that of the literature IR, with
peaks of 1089.9 cm-1; 889.38 cm-1; 758.87 of experimental one and peaks of 1091 cm -1; 893 cm-1
and 760 cm-1 of the literature values.

(1)
For other technique involving purification of salicylic acid, an experiment conducted by
suggested that ion exchange chromatography method can be used to achieve such goal.
Conclusion
The objective of this experiment is to obtain an infrared (IR) spectrometry of salicylic acid and
analyze it compared the peaks of functional groups to that of literature values from the SDBS
database. Functional groups shown in the IR spectrum include O-H phenol range from 3550-
3250 cm-1; O-H carboxylic acid from 3234.7-2400 cm -1; C=O carbonyl at peak of 1661.6 cm -1
and C=C aromatic at peaks of 1613.4 and 1484.2 cm-1. Based on the experimental results, all the
values of peaks of functional groups are match that of the literature values from the SDBS
database, the purpose of this experiment is achieved. For future direction, an ion exchange
chromatography method can be applied for purification of salicylic acid.
References

(1) Ghosh, S.N. 5 – IR Spectroscopy. Handbook of Analytical Techniques in Concrete Science

and Technology 2001, 174-204.

(2)Hsu, S.L. 20 – IR Spectroscopy. Comprehensive Polymer Science and Supplements 1989,

429-468.

Mustafa, N.R.; Kim, H.K.; Choi, Y.H.; Verpoorte, R. Single Step Purification of Salicylic Acid
from Catharanthus Roseus Cell Culture (Plant Material) by Anion Exchange for NMR Analysis.
Journal of Liquid Chromatography & Related Technologies 2008, 31(5), 702-713.
DOI: 10.1080/10826070701854469

Spectral Database for Organic Compounds (SDBS); IR spectrum; SDBS NO.: 1149;
https://sdbs.db.aist.go.jp/sdbs/cgi-bin/landingpage?sdbsno=1149 (accessed May 16, 2022).

White C.A.; G.W. Buchanan. Infrared Spectrometry. CHEM 2203/2204- Organic Chemistry
Laboratory Manual 2022-2023. pp.1-5.