Spectroscopy. Fourier Transform Infrared (FT-IR) Spectroscopy

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1 Fourier Transform Infrared (FT-IR) Spectroscopy

2 Learning objectives

3 Learning outcomes After completing this course, the student will be able to: Recognize the concept and principle of FT-IR Spectroscopy Utilize FT-IR spectroscopy in structural, qualitative and quantitative analysis of drug molecules Justify types of IR spectra Fundamental rule for FT-IR Recognize the concept of dipole moment, principle and applications Advantage and disadvantage of FT-IR spectroscopy Application of FT-IR spectroscopy Analysis with examples for the determination of pharmaceutical drugs.

4 References Organic Chemistry by John McMurry Page Number ; ; Spectroscopic methods in Organic Chemistry, Page Number 1-33; 35-73; ; Spectroscopy of Organic Compounds by P.S. Kalsi, page Fundamentals of Fourier Transform Infrared Spectroscopy by Brian C. Smith; Page Number

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6 Types of Spectroscopy Infrared (IR) spectroscopy Measures the bond vibration frequencies in a molecule and is used to determine the functional group Mass spectrometry (MS) Fragments the molecule and measures the masses Nuclear magnetic resonance (NMR) spectroscopy Detects signals from hydrogen atoms and can be used to distinguish isomers Ultraviolet (UV) spectroscopy Uses electron transitions to determine bonding patterns

7 Introduction Spectroscopy is an analytical technique which helps to determine the structure. It destroys little or no sample The amount of light absorbed by the sample is measured as wavelength is varied. 7

8 Fourier Transform Infrared (FT-IR) Spectroscopy THE ELECTROMAGNETIC SPECTRUM GAMMA RAYS X RAYS UV VISIBLE INFRARED

9 What is Infrared? Infrared radiation lies between the visible and microwave portions of the electromagnetic spectrum. Infrared waves have wavelengths longer than visible and shorter than microwaves, and have frequencies which are lower than visible and higher than microwaves.

10 What is Infrared? Humans, at normal body temperature, radiate most strongly in the infrared, at a wavelength of about 10 microns (A micron is the term commonly used in astronomy for a micrometer or one millionth of a meter). In the image to the left, the red areas are the warmest, followed by yellow, green and blue (coolest). The image to the right shows a cat in the infrared. The yellow-white areas are the warmest and the purple areas are the coldest. This image gives us a different view of a familiar animal as well as information that we could not get from a visible light picture. Notice the cold nose and the heat from the cat's eyes, mouth and ears.

11 Types of IR spectra The Infrared (IR) region is divided into three regions 1. Near region 2. Mid region 3. Far region Near-infrared refers to the part of the infrared spectrum that is closest to visible light. Far-infrared refers to the part that is closer to the microwave region. Mid-infrared is the region between these two.

12 SOURCE OF IR SPETROSCOPY The primary source of infrared radiation is thermal radiation. (heat) It is the radiation produced by the motion of atoms and molecules in an object. The higher the temperature, the more the atoms and molecules move and the more infrared radiation they produce. Any object radiates in the infrared. Even an ice cube, emits infrared.

13 Types of Electromagnetic Radiation

14 IR REGION Near region : Above 4000 cm -1 Almost entirely harmonic peaks of normal frequency Samples containing moisture can also be measure Introduced in the fields of processed foods and agriculture Mid region : 4000 to 400 cm -1 Produced information on molecular vibration and rotation Far region : Below 400 cm -1 Molecular rotation information Metal oxides, metal compounds,, organic and inorganic metal complexes.

15 Spectroscopic Methods and Quantized Transitions Molecular Effects Spectroscopic Methods Energy Ionization - > 10 4 kcal/mol Electronic Transitions UV-Vis kcal/mol Molecular Vibrations Infra-red (IR) 1-10 kcal/mol Molecular Rotations Microwave ~ 1 kcal/mol Nuclear Spin Transitions Nuclear Magnetic Resonance (NMR) 10-5 kcal/mol

16 Principles

17 Fundamental Equation

18 IR Absorption spectroscopy

19 Common methods for Drugs analysis The four most common spectroscopic methods used in organic analysis are: Method Abbrev. Energy used Units Ultraviolet-Visible Spectroscopy UV-Vis Ultravioletvisible nm Infrared Spectroscopy IR Infrared mm or cm -1 Nuclear Magnetic Resonance NMR Radio frequencies Mass Spectroscopy MS Electron volts Hz amu

20 What actually happens to the sample during an analysis?{how do the sample and energy interact} Matter/Energy Interactions What happens when a sample absorbs UV/Vis energy? Excitation of ground state electrons UV/Vis (typically p and n electrons) E electronic increases momentarily Mo mentarily ( 200 nm) p* sample p p* transition p What happens when a sample absorbs IR energy? Stretching and bending of bonds (typically covalent bonds) E vibration increases momentarily -O-H IR ( 3500 cm -1 ) -O H

21

22 Energy levels in Infrared Absorption hn n 3 n 2 n 1 n 0 Infrared Absorption and Emission h(n 1 - n 0 ) h(n 2 - n 1 ) (overtone) h(n 1 - n 0 ) Excited states Ground (vibrationa l) states Infrared absorption occurs among the ground vibrational states. The energy differences, and corresponding spectrum, determined by the specific molecular vibration(s). The infrared absorption is a net energy gain for the molecule and recorded as an energy loss for the analysis beam.

23 Dipole Moment A dipole moment is a measurement of the separation of two oppositely charged charges Absorption strength depends on the size of deformation of the dipole moment due to vibration

24 Infrared light and a molecule only interact when the dipole moment of the molecule changes due to vibration

25

26 Infrared Spectroscopy The bonds between atoms in the molecule stretch and bend, absorbing infrared energy and creating the infrared spectrum. Symmetric Stretch Antisymmetric Stretch Bend A molecule such as H 2 O will absorb infrared light when the vibration (stretch or bend) results in a molecular dipole moment change

27

28 Example Which of the following atoms or molecules will absorb IR radiation: H Cl H 2 N 2 Cl 2 Why?

29 The number of normal frequencies of a molecules consisting of n atoms can be determined by the following formula:

30 Infrared Spectroscopy (Water Molecule) A molecule can be characterized (identified) by its molecular vibrations, based on the absorption and intensity of specific infrared wavelengths.

31 Infrared Spectroscopy Infrared Spectroscopy (Isopropyl alcohol) For isopropyl alcohol, CH(CH 3 ) 2 OH, the infrared absorption bands identify the various functional groups of the molecule

32 Absorption position

33 Absorption position

34 Finger print region The region below 1500 cm -1 is rich in many absorptions which are caused by bending vibrations. In the spectrum, the number of bending vibrations is usually more than the number of stretching vibrations. This regions is called Finger print region. Some substances containing the same functional group show similar absorptions above 1500 cm-1 but their absorption position differ in the finger print region. Such compounds can be easily distinguished by comparing their finger print regions. Infrared spectroscopy (IR) measures the bond vibration frequencies in a molecule and is used to determine the functional group

35 Transmittance (%) Spectroscopy IR Correlation Diagram Region I cm -1 O-H N-H C-H bond stretching Alcohols Phenols Carboxylic acids Amines Amides Region II cm -1 C=O Acid chlorides Anhydrides Esters Ketones Aldehydes Carboxylic acids Amides Fingerprint Region (below 1500 cm -1 ) 0 Alkynes Alkenes Alkanes C-H =C-H -C-H Frequency (cm -1 ) / Wavelength (microns, mm)

36 A summary of the principle infrared bands and their assignments. R is an aliphatic group. Functional Group Type Frequencies cm-1 Peak Intensity C-H sp3 hybridized R3C-H M(sh) sp2 hybridized =CR-H M(sh) sp hybridized C-H 3300 M-S(sh) aldehyde C-H H-(C=O)R 2750, 2850 M(sh) N-H primary amine, amide RN-H2, RCON-H2 3300, 3340 S,S (br) secondary amine, amide RNR-H, RCON-HR S (br) O-H alcohols, phenols free O-H W(sh) hydrogen bonded S(br) carboxylic acids R(C=O)O-H S(br) CN nitriles RCN S(sh) CC acetylenes R-CC-R W(sh) R-CC-H M(sh) C=O aldehydes R(C=O)H S(sh) ketones R(C=O)R S(sh) esters R(CO2)R S(sh) anhydrides R(CO2CO)R 1820, 1750 S, S(sh) carboxylates R(CO2)H 1600, 1400 S,S(sh) C=C olefins R2C=CR W(sh) R2C=CH M(sh) R2C=C(OR)R S(sh) -NO2 nitro groups RNO2 1550, 1370 S,S(sh)

37 Analysis Targets Compound: Organic and Inorganic compounds State: Gas, Solid and Liquid Analysis description Qualitative analysis Functional group analysis : How many function groups present in the compounds with respect to the data Pattern analysis: What is the materials by comparing standard spectra Quantitative analysis From the absorption we can determine the concentration Finger print preparation Quantitative analysis

38 Types of Transmission Technique Solid samples

39 Liquid samples

40 KBr Pellet Technique

41 KBr Pellet Technique

42

43 Instrumentation Perkin Elmer TM Spectrum One BRUKE TENSOR TM Series

44 Thin film Technique

45

46

47 Real Chromatogram for liquid samples

48 Gas cell The gaseous samples are imported because one can in some cases see also the rotational fine structure of the absorption bands. The sample gas is placed in a gas cell at low temperature and pressure Gas cell

49 Real Chromatogram of Gas sample

50 Diagram of IR spectroscopy

51 Light source FTIR seminar FT Optical System Diagram He-Ne gas laser (ceramic) Movable mirror Beam splitter Sample chamber (DLATGS) Interferometer Fixed mirror Detector

52 Signal strength Spectroscopy Interference of two beams of light Movable mirror Fixed mirror A Movable mirror Same-phase interference wave shape -2l -l 0 l 2l Fixed mirror Continuous phase shift B Movable mirror Opposite-phase interference wave shape I (X) Fixed mirror C Movable mirror -2l -l 0 l 2l 0 l Same-phase interference wave shape D Interference pattern of light manifested by the optical-path difference

53 Interference is a super positioning of waves Relationship between light source spectrum and the signal output from interferometer Light source spectrum I Signal output from interference wave (a) Monochromatic light A z Wavenumber u S I Time t (b) Dichroic light SA z (c) Continuous spectrum light b (u) Wavenumber u I(t) Time t Wavenumber u All intensities are standardized. Time t

54 FT-IR Advantages 1. Better sensitivity and brightness - Allows simultaneous measurement over the entire wavenumber range - Requires no slit device, making good use of the available beam 2. High wavenumber accuracy - Technique allows high speed sampling with the aid of laser light interference fringes - Requires no wavenumber correction - Provides wavenumber to an accuracy of 0.01 cm-1 3. Resolution - Provides spectra of high resolution 4. Stray light - Fourier Transform allows only interference signals to contribute to spectrum. - Background light effects greatly lowers. - Allows selective handling of signals limiting intreference 5. Wavenumber range flexibility - Simple to alter the instrument wavenumber range CO2 and H2O sensitive

55 Capabilities of Infrared Analysis Identification and quantitation of organic solid, liquid or gas samples. Analysis of powders, solids, gels, emulsions, pastes, pure liquids and solutions, polymers, pure and mixed gases. Infrared used for research, methods development, quality control and quality assurance applications. Samples range in size from single fibers only 20 microns in length to atmospheric pollution studies involving large areas.

56 Applications of Infrared Analysis Pharmaceutical research Forensic investigations Polymer analysis Lubricant formulation and fuel additives Foods research Quality assurance and control Environmental and water quality analysis methods Biochemical and biomedical research Coatings and surfactants Etc.

57 Which is the following compounds a-d has an IR absorption at 3400 cm -1?

58 A strong absorption signal at 1650 cm -1 in an IR spectrum indicates the presence of a b. What is the structure of the compound that gives the following IR spectrum? C. a. CH 3 -CH 2 -C C-H b. CH 3 -CH 2 -OH c. CH 3 -CH 2 -C C-H d. CH 3 -CH 2 -CH 2 -NH 2

59 A strong absorption signal at 3400 cm-1 in an IR spectrum indicates the presence of a. CH 3 CH 2 OH b. (CH 3 ) 2 CHCN c. CH 3 CH 2 OCH 2 OCH 2 CH What is the structure of the compound that gives the following IR spectrum? a. CH 3 OH b. CH 3 CH 2 CH=O

60 The molecular formula C 8 H 11 O that is consistent with the IR spectrum below is

61 The structure of the compound that gives the infrared (IR) spectrum below is

62 %T Spectroscopy cm cm W av enu mber s ( cm- 1)

63 %T Spectroscopy cm cm cm W av enu mber s ( cm- 1)

64 %T Spectroscopy cm cm W av enu mber s ( cm- 1)

65 %T Spectroscopy W av enu mber s ( cm- 1)

66 %T Spectroscopy W av enu mber s ( cm- 1)

67 %T Spectroscopy W av enu mber s ( cm- 1)

68 %T Spectroscopy C-O W av enu mber s ( cm- 1)

69 %T Spectroscopy F W av enu mber s ( cm- 1)

70 %T Spectroscopy G W av enu mber s ( cm- 1)

71 %T Spectroscopy W av enu mber s ( cm- 1)

72 %T Spectroscopy W av enu mber s ( cm- 1)

73 %T Spectroscopy W av enu mber s ( cm- 1)

74

75 Why water cannot be used as solvent in IR spectroscopy? Water is IR active so produces a peak due to it OH group at 3500cm-1 this is why equipment should be keep in oven Why KBr is used to prepare the IR samples. What is the difference of UV and IR

76 Deduce the structure of an unknown compound with molecular formula C5H12O using information given by its infrared spectrum. Intensity (peak): Frequency (cm 1): s 3300 d 2800 t 2700 s 1465 s 1450

77 Deduce the structure of an unknown compound with molecular formula C9H10O using information given by its infrared spectrum. Intensity (peak): Frequency (cm 1): s 2900 m 2800 s 1600 m 1475

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