Spectrochemical Method of Analysis (CHM 580)

EXPERIMENT 1 :Qualitative analysis of aspirin phenacetin

caffeine and sample using FTIR and NMR

DATE OF EXPERIMENT : 2/4/2019

DATE OF SUBMISSION :23/5/2019

NAME : NUR BATRISYIA HAZIRAH BT MOHAMMAD

MATRIC NO : 2017411816

COURSE : AS2023M3

GROUP : 1) NUR FATEMA BT YATIRAN

2) NUR NABILAH BT NUSRI

It is my responsibility as a student of UiTM to adhere the truthfulness and

avoid dishonesty, fraud, or deceit any type of connection into write up and
conduct of this experiment.

Signature:

Date:
TITLE :
Qualitative analysis of aspirin phenacetin caffeine and sample using FTIR and NMR

ABSTRACT
In the experiment the objective for FTIR is to identify functional groups in IR
spectra of standard compounds Aspirin, Phenacetin, Acetyl Salicylic Acid and
Caffeine. Other than that to identify functional groups present in an unknown sample.
For NMR the objectives are to identify major peaks in NMR spectra of standard
compounds of Aspirin, Phenacetin, Caffeine and Acetylsalicylic acid and to predict
the chemical structure of unknown sample using both data from FTIR and NMR
technique. Four standards and one unknown sample b ware analyzed by using
peletting method for FTIR. The standards and sample also analyzed using NMR
instrument so that the peak can be identified.

INTRODUCTION
Infrared spectroscopy (IR spectroscopy) is the spectroscopy cope with the
infrared region of the electromagnetic spectrum. Infrared spectroscopy however has
light that have longer wavelength but higher frequency than visible light. It covers a
range of techniques, mostly based on absorption spectroscopy. As with all
spectroscopic techniques, it can be used to identify and study chemicals functional
groups.

Nuclear Magnetic Resonance (NMR) spectroscopy is an technique used in quality

controland reserach for determining the content and purity of a sample as well as
its molecular structure. For known compounds NMR can quantitatively analyze
mixtures contained the compounds. NMR can either be used to match against spectral
libraries or to infer the basic structure directly for unknown compounds.
LITERATURE REVIEW

Infrared spectroscopy is one of the most important analytical techniques available

to as the infrared spectroscopy is that any sample in any state can be analyzed
virtually. As an example, liquids, solutions pastes powders films and fibres gases and
surfaces can be examined with sampling technique.

Fourier transform infrared spectroscopy (FTIR) has faciliated different sampling

techniques includes attenuated total reflection and diffuses reflectance infrared. The
analysis of infrared light interacting with a molecule is named as infrared
spectroscopy. By measuring absorption, emission and reflection the infrared can be
measured in 3 different ways.

Mainly used in organic and inorganic chemistry as it is used to determine

functional groups in molecules. IR Spectroscopy measures the vibrations of atoms,
and based on this it is possible to determine the functional groups Generally, stronger
bonds and light atoms will vibrate at a high stretching frequency (wavenumber).

Nuclear magnetic resonance (NMR) spectroscopyis a technique used in quality

control and research to determine its content and purity and molecular structure. For
unknown compounds NMR can be used by comparing with spectral libraries to know
its basic chemical structure.

Once it is known NMR is used to determine molecular confrontational exchange

as well as studying physical properties to get a better result variety of NMR
techhniques can be used.
EXPERIMENTAL
Sample : Unknown B (Ascorbic Acid)
List of chemicals used :
1. Aspirin
2. Caffeine
3. Phenacetin
4. Acetyl Salicylic Acid
5. Unknown sample B
6. KBr powder
7. Sodium chloride cell
8. Deuterated chloroform CDCl3
List of apparatus used :
1. Mortar
2. Pestle
3. Spatula
4. Kbr handpress
5. Sample holder
6. Pasteur pipet
7. Conical vial
8. NMR tube
Instrument used :
FTIR : Perkin Elmer precisecy spectrum one FTIR spectrometer
NMR : NMR spectrometer
Experimental procedure :
FTIR
A. Mixing of sample and KBr
The agate mortar and pestle was removed from desiccator in the fume hood. 1 mg
of solid sample was grinded in agate mortar into powder for about 1 minute. 80 mg of
of KBr powder was added into the sample powder and grinded for about 30 seconds
with pestle. The mixture was scrape into the middle with a spatula and the mixture
was grinded again for about 15 seconds. The mixture was heap in the centre of
mortar.
B. Preparation of KBr pallets
 One fourth of the KBr mixture took and transfered into the collar of the
handpress. The die set was lifted carefully and the handle was opened and closed. The
dial pressure was rotated until the upper ram of the handpress slightly touched the
upper anvil on the die assembles. the unit was tilted back in order to hold from fall.
The mixture was slowly compressed and the pallet was inspected by the FTIR
instrument. It is then repeated with other solid sample.

NMR
A. Determination of the spectrum of each separate component
30 mg of aspirin, phenacetin and caffeine was weighted approximate to 30 mg in
different conical vial. 0.5 ml of deuterated cloroform CDCl3 was transfered with a
clean nd dry pasteur pipet to sample. The conical vial was swirled so that the sample
solid was completely dissolved. The solution was transfered into clean and dried
NMR tube. Once the solution has been transfered, some CDCl3 was added to bring
the total solution height to about 4 cm from bottom and its was capped then the tube
was analysed by the NMR instrument. It is then repeated with other solid sample and
unknown sample.

RESULT
FTIR
Table 1: Functional group exist in caffeine
Vibration Literature Wave number Experimental wave
(cm−1) number (cm−1)
1) C-H stretching 3000-2840 2955.21
2) C=O tertiary amide 1680 1698.78
3) C=C cyclic alkene 1650-1566 1660.63
4) C-N stretching 1250-1020 1239.81
5) C=N 1690-1630 1660.63
Table 2: Functional group exist in Acetyl Salicylic acid
Vibration Literature Wave number Experimental wave
(cm−1) number (cm−1)
1) O-H stretching carboxylic 3300-2500 3300-2500
2) C=C aromatic 1600-1400 1419.84
3) C-H stretch aromatic 3000-2840 2997.11
4) C=O ester 1750-1735 1755.06
5) C=O carboxylic 1760 1755.06
6) Benzene overtone 2000-1650 2000-1650
7) C-O 1000-1300 1219.84
8) OOP C-H ortho 860-680 790.35

Table 3: Functional group exist in Aspirin

Vibration Literature Wave number Experimental wave
(cm−1) number (cm−1)
1) O-H stretch carboxylic 3300-2500 3300-2500
2) C=C aromatic 1600-1400 1370.31
3) C-H stretch aromatic 3000-2840 2916.95
4) C-H bending 755 ± 20 755.53
5) C=O carboxylic 1760 1754.50
6) C-O 1000-1300 1013.19
7) Benzene overtone 2000-1650 2000-1650
8) OOP C-H ortho 860-650 840.34

Table 4: Functional group exist in Phenacetin

Vibration Literature Wave number Experimental wave
(cm−1) number (cm−1)
1) C=C aromatic 1600-1400 1606.36
2) C=O secondary amide 1680 1659.68
3) C-O-C stretch 1250-1050 1245.22
4) N-H stretch 3500-3350 3286.59
5) C-N 1342-1266 1266.51
6) Oop C-H aromatic 810 ± 20 826.08
7) CH2 1480-1440 1447.93
8) Benzene overtone 2000-1650 2000-1650
9) C-H stretch aromatic 3000-2840 2805.68
10) C-H stretch aliphatic 690-900 838.31

Table 5: Functional group exist in sample B (Ascorbic Acid)

Vibration Literature Wave number Experimental wave
(cm−1) number (cm−1)
1) O-H stretch 3600-3200 3600-3200
2) C=O ester 1750-1720 1755.12
3) C=C 1680-1600 1672.87
4) CH3 bending 1480-1440 1458.64
5) OH carboxylic 3600-2500 3600-2500
6) C-H stretch aromatic 3000-2840 2917.56
7) C-H stretch 690-900 756.81

NMR
Table 6: Spectra of caffeine
 Structure Chemical Shift Multiplicity Integral
Literature Experimental
(CO)2NCH3 2-3 2.49 singlet 3H
R-N-CH3 2.3-3.0 3.19 singlet 6H
N-CH=N 7.5-8.3 8.05 singlet 1H

Table 7: Spectra of Acetyl Salicylic Acid

Structure Chemical Shift Multiplicity Integral
Literature Experimental
-COCH3 2-3 2.28 doublet 3H
C6H42R 6.5-7.7 7.20-7.94 quartet 4H
-COOH 10-13 - singlet 1H

Table 8: Spectra of Aspirin

Structure Chemical Shift Multiplicity Integral
Literature Experimental
-COCH3 2-3 2.26 doublet 3H
C6H42R 6.5-7.7 7.22-7.94 quartet 4H
-COOH 10-13 13.16 singlet 1H

Table9 : Spectra of Phenacetin

Structure Chemical Shift Multiplicity Integral
Literature Experimental
-COCH3 2-2.3 2.02 singlet 3H
N-H 1-9 1.28 singlet 1H
C6H42R 6.5-7.5 6.83-7.45 doublet 2H
O-CH2 3-4 3.98 singlet 4H
O-CH2 3-4 3.36 singlet 3H

Table 10 :Spectra of Sample B (Ascorbic Acid)

Structure Chemical Shift Multiplicity Integral

H-COO 2.53 singlet 0.78≈1H

-R-O-CH2 3.43 singlet 2H
-O-C2R-H 3.73 singlet 1H
OH-CR-C-OH 4.73 singlet 2H
OH-CR=CR-OH 4.92 singlet 2H
DISCUSSION
In this experiment four standards phenacetin, aspirin, acetyl salicylic acid
caffeine and one unknown sample which is sample B. Caffeine is known as natural
stimulant which helps to reduces fatigue and helps people to concentrate. It also
increases the activity of brain through its action. It consists functional groups as
shown in table 1 such as C=O tertiary amide with experimental wave number of . the
peak that produces from the IR spectra comes from the vibration of molecules which
emits the frequency. From the NMR results as in table 6 the chemical structure
existed at NMR chemical shift was observed.

Acetyl salicylic acid and aspirin is the same as it is the derivative of salicylic acid
that is mild, non-narcotic analgesic useful in the relief of headache and muscle and
joint aches. It is also effective for treatement of fever, mild infection and etc. Acetyl
salicylic acid and aspirin functional groups was presented as in table 2 &3. from the
NMR results the signal of COOH of aspirin can be observed while at acetylsalicylic
acid the peak can’t be seen.
Phenacetin is a widely used analgesic however it has beeb declined due to the
adverse effect in IR has the most functional group existed compared to others. The
variation of C-H bond from aromatic aliphatic and presence of N-H bond. For the
NMR chemical shift the compound was discovered to have 5 chemical structure that
produce shifts.

From the IR and NMR reading of the standard. Unknown sample B was also
observed the functional groups and chemical shifts that happen from the peak
observed.

CONCLUSION
In conclusion all four standards and unknown sample B was analyzed
by using FTIR and NMR to identify its functional group and major peaks.
By observing both spectras, its found out that unknown B is Ascorbic
Acid.

REFERENCES
1. Docdownloader.com_chm-580-exp-1-amp-7.pdf

2. https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Tex
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scopy/Vibrational_Spectroscopy/Infrared_Spectroscopy

3. https://pubs.acs.org/doi/pdf/10.1021/ac60064a002

4. https://www.researchgate.net/publication/331233738_Fourier_Transform_Infrared
_Spectroscopy_Fundamentals_and_Application_in_Functional_Groups_and_Nanoma
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