Presentation is loading. Please wait.

Presentation is loading. Please wait.

Name: Anil kumar Appapurapu College: Bapatla college of pharmacy, Bapatla. Year: M. Pharmacy, 2nd year. Profile link:

Similar presentations


Presentation on theme: "Name: Anil kumar Appapurapu College: Bapatla college of pharmacy, Bapatla. Year: M. Pharmacy, 2nd year. Profile link:"— Presentation transcript:

1 Name: Anil kumar Appapurapu College: Bapatla college of pharmacy, Bapatla. Year: M. Pharmacy, 2nd year. Profile link: appapurapu Name: Dr. T.E.G.K. Murthy, M Pharm, Ph.D. College:Bapatla College of Pharmacy Profile link: AuthorCo-author 1 BCPE03

2 The challenging scenario in the aspects of efficacy, safety, purity, and quality determination of the drug samples became optimistic. Drug 1 Natural ---animal ---- plants ----marine Synthetic ----organic ----in-organic Chemical / functional Group interaction 2 Signal transduction 1 Therapeutic effects 1 Molecular basis 2 sources 1 Importance of analysis of drugs Analysis basis Drug –receptor interaction B Sue Brizuela,Ms, Judith A Hesp, MS, “Drug Information” Remington: The science and practice of pharmacy,19 th edition,volume.1, Mack publishing company Easton, Pennsylvania18042, print. 2. B.K. SHARMA," fundamental principles of spectroscopy”,spectroscopy,20th edition, Goel publications, Delhi, print.

3 Analysis Structure.breakdown ANALYSIS 1.Separation techniques 2.Spectrophotometric 3. Electro analytical 4. Titrimetric analysis chromatography Potential & conductometry Titrations 1.uv-visible 2.Infra red 3.Mass 4.Neclear magnetic resonance Classification of analytical techniques Douglas A.Skoog, F.James Holler, Timothy A.Nieman,,”introduction to instrumental methods of analysis", principles of instrumental analysis, 5 th edition, saunders Golden sunburst series. Forth worth, Philadelohia, Chicago, Sydney, Toronto. Reprint Print. 3

4 Spectroscopy [2,4,5] EMR ANALYTE SPECTROPHOTOGRAPH Conc. should be lower 1.UV-Visible radiations---excitation of electrons----uv-visiblespectrum 2.IR-radiations—vibration changes in electrons---IR spectrum 3.Microwave radiations---spin resonance----E.S.R spectrum 4.Radio frequency---spin rotational changes---N.M.R spectrum study of interaction of electromagnetic radiation with matter 4.www.answers.com. Web. 25 feb www. en.wikipedia.org. Web. 25 feb en.wikipedia.orghttp://en.wikipedia.org/wiki/Infrared_spectroscopy 2. B.K. SHARMA," fundamental principles of spectroscopy”,spectroscopy,20 th edition, page noS-11, Goel publications, Delhi, print. 4 Principle of spectroscopy [2,4,5]

5 Gamma rays X rays UV Visible Infra-Red Micro waves Radio waves Violet indigo Blue Green Orange Yellow Red 370 nm EMR Drug substance Energy Kcal/mol 9.4 x x x x x x x Λ0AΛ0A Frequency (Hz) Absorbing radiations Type of spectroscopy x x x Emission Both E & Abs NMR Abs Absorption THE ELECTROMAGNETIC SPECTRUM Characteristics of radiations Resulting spectrum 5. www. en.wikipedia.org. Web. 25 feb en.wikipedia.orghttp://en.wikipedia.org/wiki/Infraredspectroscopy 2. B.K. SHARMA," fundamental principles of spectroscopy” Spectroscopy 20 th edition, page no.S-11- S-20, goel publications, Delhi, 2007.print. 5 [2,5]

6 IR -SPECTROSCOPY 2 Theory origin of spectra Physics 3 Principle observed changes Chemistry 2 Instrumentation working Engineering 6 Applications [2,3,6] uses pharmacy BIO-technology Genetic engineering Multidisciplinary of IR spectroscopy [2,3,6] 6 2. B.K. SHARMA," Infrared spectroscopy” Spectroscopy 20th edition, page no.S-220, goel publications, Delhi, 2007.print. 3. Douglas A.Skoog, F.James Holler, Timothy A.Nieman,,”Infrared spectroscopy", principles of instrumental analysis, 5 th edition, saunders Golden sunburst series. Forth worth, Philadelohia, Chicago, Sydney, Toronto. Page no Print. 6. Hobart H. Willard, Lynne L. Merritt. Jr., John A. Dean, Frank A. Settle, Jr. “Infrared spectroscopy”, instrumental methods of analysis,7 th edition page288,289,292,293, content no CBS publications, Toronto print.

7 REGIONWAVE LENGTH λ (μm) WAVE NUMBER υ (cm -1 ) FREQUENCY RANGE Hz NEAR x x10 14 MIDDLE x x1 12 FAR x x10 11 MOST USED x x10 13 IR-REGION: 12, cm -1 1.Near IR----carbohydrates and proteins 2.Middle IR-----organic molecules—functional groups 3.Far IR—in-organic –co-ordination bonds& quaternary ammonium compounds 3. Douglas A.Skoog, F.James Holler, Timothy A.Nieman,,”Infrared spectroscopy”, introduction to instrumental methods of analysis", principles of instrumental analysis, 5 th edition, saunders Golden sunburst series. Forth worth, Philadelohia, Chicago, Sydney, Toronto. Page no Print. 6. Hobart H. Willard, Lynne L. Merritt. Jr., John A. Dean, Frank A. Settle, Jr. “Infrared spectroscopy”, instrumental methods of analysis,7 th edition page288,289,292,293, content no CBS publications, Toronto print. [3,6] 7

8 REGION DetectorsSource of radiation Optical system Type of samples NEAR Photo conductance Tungsten filament lamp Prism grating Solid / liquid MIDDLE Thermal typeNernst glowers/ Nichrome wire Diffraction grating Liquid / gas FAR Golay, pyroelectric High pressure mercury lamp Double beam grating Gas MOST USED Thermal typeNernst glowers/ Nichrome wire Diffraction grating Liquid / gas Type of analysis measurement Qualitative Quantitative Diffusive reflectance Absorption Qualitative Quantitative Chromatographic Diffusive reflectance Absorption Adsorption Quantitativeemission Qualitative Quantitative Chromatographic Diffusive reflectance Absorption Adsorption INSTRUMENTAL AND APPLICATIONS OF VARIOUS IR REGIONS [7,8] 7. www. orgchem.colorado.edu. web, Donald L.Pavia, Gary M.Lampman, George S. Kriz.”infrared spectroscopy "introduction to spectroscopy,3 rd edition, CBSPublications Thomas books Australia, U.S.print,Canada, Mexico, print.. 8

9 Due to 4 changes in energies of the molecules 1. Electronic transitions -----E t 2. Electronic rotations E r 3. Electronic vibrations E v 4. Electronic energy E e total energy of the molecule= E e + E v + E r + E t energies required in the order E e > E v > E r > E t Various types IR –spectra 1. Rotational spectra 2. Vibrational- rotational spectra 3. Electronic band spectra ORIGIN OF IR SPECTRUM [2,3] 2. B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. 3. Douglas A.Skoog, F.James Holler, Timothy A.Nieman,”Infrared spectroscopy”, introduction to instrumental methods of analysis", principles of instrumental analysis, 5 th edition, saunders Golden sunburst series. Forth worth, Philadelohia, Chicago, Sydney, Toronto. Page no Print. 9

10 Differences between various types of IR spectra 2,(a,b,c) Character Electronic band spectra a Vibration- rotational spectra b Rotational spectra c 1. IR region Near IR Middle IR Far IR 2.Energy required Higher less very less 3.Dipole moment less induced Definite dipoleIntense dipole 4.Sample stateSolidsLiquids / gases Only gases 5.Thoery supportingFrank codon principle Harmonic oscillator principle Rigid rotor principle 6.Changes observedExcitation, vibration Vibration, rotationOnly rotation 7.Highly feasible for single bonds double bondsTriple bonds 2. B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. a.S-234 to s-249 b. s-220 to s- 234 c. s-201 to s

11 1. Selection rules 9 2. Types of vibrations 9 3. Number of possible vibrational modes Vibrational frequency [9,10] 5. Factors influencing vibrational modes [9,10] INFRARED THEORY [9,10] Matching of Frequency Dipole moment Vibrational Quantum Number Translational motion Rotational motion Vibrational motion A. Phase and solvents used B. Coupled interactions C. Hydrogen bonding D. Fermi resonance E. Electronic effects 9. Robert M.Silverstien Francis X.Webster,”infrared spectroscopy”, spectroscopic identification of organic compounds, 6 th edition, John Wiley, Chichester, Singapore, Toronto, Brisbane page no. 3.5, Print. 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2 nd edition,Narosa,Newdelhi, Chennai Print. 11

12 Asymmetric ( nu) Symmetric ( nu) Scissoring ( s) Rocking (ρ ) Wagging (ω) Twisting (tau) Stretching vibrationsBending vibrations In-planeOut -plane cm -1 In-plane Types of vibrations [5,11] Vibrational energy depends on :- 1. masses of the atoms 2. strength of bonds 3. arrangement of atoms within the molecule 5. www. en.wikipedia.org. web.25 feb en.wikipedia.orghttp://en.wikipedia.org/wiki/Infrared_spectroscopy 11. Dudles H,Williams,Ian Fleming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, Print. 12 For stretching vibration = N -1 For bending vibration [(3N - 6)-(N -1)]=2N -5 for non-linear [(3N - 5)-(N -1)] =2N – 4 for linear ‘N’ is the number of atoms in the bond.

13 M1 Force constant, k M2 Ball and spring representation of 2 atom of molecule vibrating in the direction of bond Vibrational frequency 2 Factors influencing absorption frequency 2  Masses of attached atoms. As masses increase, wave number decreases.  Strength of chemical bond. As bond strength increases, wave number increases.  Hybridization. Bonds are stronger in the order sp > sp 2 > sp 3.  Resonance. Conjugation lowers the energy to vibrate bond. 2. B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. 13

14 A. Phase and solvents used Phase and solvents may bring the changes in IR in the aspects of 1.Band frequency shifts cm -1 in vapor state cm -1 in liquid state 2. Band splitting e.g.;- the effect of phase and solvents in Acetone. >c=o in acetone cm -1 in vapor state cm -1 in liquid state Acetone interactions with some solvents cm -1 in a solution of Hexane cm -1 in chloroform cm -1 in ethanol Acetone interactions with some solvents cm -1 in a solution of Hexane cm -1 in chloroform cm -1 in ethanol Dipole-dipole lowers wave number Factors influencing vibrational modes [2,10,12] 2. B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2 nd edition,Narosa,Newdelhi, Chennai Print. 12.Y.R.Sharma,”infrared spectroscopy”, Elementary organic spectroscopy principles and chemical applications, first edition 1980, reprint print. 14 B. Coupled interactions Extent of coupling influenced by 1.stretching vibrations with two vibrations have common atom 2. bending vibrations with a common bond b/t vibrating groups. 3. coupled groups of identical energies. 4. groups separated by two/more bonds, little or no interaction occur. 6. vibrations of symmetrical species.

15 Factors influencing vibrational modes [2,10,12] 2. B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2 nd edition,Narosa,Newdelhi, Chennai Print. 12.Y.R.Sharma,”infrared spectroscopy”, Elementary organic spectroscopy principles and chemical applications, first edition 1980, reprint print. 15 Strength of H-bond effected by 1. ring strain 2. molecular geometry 3. relative acidity and basicity of proton donor and acceptor C.. Hydrogen bonding Types of hydrogen bonding :- 1. intermolecular hydrogen bonding extent of bonding depends on Temp. 2. intramolecular hydrogen bonding D. Fermi resonance Factors leads to Fermi resonance a) vibrational levels are same for symmetrical compounds. b) interacting groups located in the molecule for an appreciable mechanical coupling to occur. e.g.:- cm-1 the splitting caused by coupling b/t fundamental c=o stre. near 1340 cm -1 and 667 cm cm -1 1 st overtone 1. co 2 actual absorption frequencies at 1286,1388 cm-1 the splitting caused by coupling b/t fundamental c=o stre. near 1340 cm -1 and 667 cm cm -1 1 st overtone 2. lactones, lactims, lactums, aldehydes.

16 Factors influencing vibrational modes [2,10,12] 1.Inductive effect —introduction of alkyl group length 2.Mesomeric effect bond strength 3.Field effect. force constant vibrational frequency E. Electronic effects ► Lone pair of electrons ► conjugation lowers absorption ► Mesomeric effect dominate inductive effect for some time and vice versa Introduction of electronegative atoms Bond strength Force constant Vibrational frequency cm-1 HCHO cm-1 cm-1 CH 3 CHO cm-1 cm-1 CH 3 COCH cm-1 cm-1 ClCH 2 COCH cm-1 cm-1 Cl 2 CHCOCH cm B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2 nd edition,Narosa,Newdelhi, Chennai Print. 12.Y.R.Sharma,”infrared spectroscopy”, Elementary organic spectroscopy principles and chemical applications, first edition 1980, reprint print.

17 INSTRUMENTATION [2,6] 1.Radiation source 2. Monochromatic light. 3.Sample handling. 4.Detectros 5.Amplifiers. 2. B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. 6. Hobart H. Willard, Lynne L. Merritt. Jr., John A. Dean, Frank A. Settle, Jr. “Infrared spectroscopy”, instrumental methods of analysis,7thedition content no CBS publications, Toronto print Sampling of substances solids liquids gases. 1.solids run in solution form 2.solid films 3.mull technique 4.pressured pellet technique.

18 S.NOCharacterNernst glower GlobarIncandescentMercury arcTungsten lamp Co 2 laser 1.CompositionRare earth oxides Silicone carbide Nichrome wireHigh (Hg) pressure Tungsten – Halogen Tunable Co 2 laser. 2.Operating temp — 2200K K 1100K1000K3500K Radiations produced O.P cm-1 12, cm-1 cm cm-1 cm-1 10, cm-1 cm-1 < 665 cm-1 cm-1 10,100—4000 cm-1 cm cm-1 4.IR region usedNear / visible Middle Near Far MiddleMiddle /near 5.Intensity of radiation More intenseAs equal to Nernst Less but longer life. Greater MildMore effective 6.Out put significant (λ) >2µm >5µm 2-4µm 10µm 2-4µm 5 µm 7.Used forCarbohydrate, protein Simple Functional groups complex organic molecules. In- organic complexes. Most organic functional groups NH 3 C 6 H 6, C 2 H 5 OH INFRARED SOURCES [3,6] 3.Douglas A.Skoog, F.James Holler, Timothy A.Nieman,,”Infrared spectroscopy", principles of instrumental analysis, 5 th edition, saunders Golden sunburst series. Forth worth, Philadelohia, Chicago, Sydney, Toronto. Page no Print. 6. Hobart H. Willard, Lynne L. Merritt. Jr., John A. Dean, Frank A. Settle, Jr. “Infrared spectroscopy”, instrumental methods of analysis,7 th edition page288,289,292,293, content no CBS publications, Toronto print. 18

19 S.No Character Thermocouple or Thermopile Thermister or Bolometer Pyroelectric Golay or Pneumatic 1.PrinciplePelletier effectWhetstone bridgeElectric polarization Expanction of gases 2.Materials usedBismuth & Antimony, coated by metal oxides Sintered oxides of Mn, co, Ni TGS, DTGS, LiTGO 3, LiTubO 3 generally CO 2 3.Material should beThermally activeThermally sensitive resistors Non-center symmetric crystal Inert nature 4.DescriptionHalf -junction- hot Alternate -junction -cold Metal cylinder closed in b/t metal plate & Ag 5.Conversion unitRadiant to Electric signal ---measured Change in resistance - Q Thermal alteration to E.polarization Expanction of gas to pressure to e.signal 6.UsedPhotocuastic spectroscopy Diffusive reflectance FTIRNon –dispersive IR 7.Response time 30 sec4 sec multiple scanning0.01sec DETECTORS or TRANSDUCERS [3,6] 3.Douglas A.Skoog, F.James Holler, Timothy A.Nieman, “ Infrared spectroscopy”, introduction to instrumental methods of analysis, principles of instrumental analysis, 5 th edition, saunders Golden sunburst series. Forth worth, Philadelohia, Chicago, Sydney, Toronto. Page no Print. 6. Hobart H. Willard, Lynne L. Merritt. Jr., John A. Dean, Frank A. Settle, Jr. “Infrared spectroscopy”, instrumental methods of analysis,7 th edition page288,289,292,293, content no CBS publications, Toronto print. 19

20 ► 3600—3000cm -1  C-H. ---OH, --NH 2, >NH,  C-H. ► 3200—3000cm -1  C-H, Ar— C-H. ►3000—2500 cm -1 --C—H of methyl/methelene asymmetric stre. --C—H, --COOH ►2300—2100 cm -1 Alkynes Cyanides 2260—2200 Isocyanides 2280—2250 ►1900—1650 cm -1 strong bands--- >c=o —1760 anhydrides Imides two broad band at 1700 Functional [11,13] group region 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print. 13.Harold F.Walton,Jorge Reyes, "infrared spectroscopy", Modern Chemical Analysis And Instrumentation,IMBD, Mumbai, Reprint 2001page no Print. 20 General guidelines for IR [11,13]

21 ► cm -1 confirms --- esters, alcohol, ethers. Nitro ► 1000—800 cm -1 C— Cl, C-Br ► 800—710cm -1 meta substituted benzene ► 770—730cm -1 strong mono substituted benzene. ► 710—665cm -1 ortho, Para, benzene. Finger print region [11,13] 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print. 13.Harold F.Walton,Jorge Reyes, "infrared spectroscopy", Modern Chemical Analysis And Instrumentation,IMBD, Mumbai, Reprint 2001page no Print. 21 General guidelines for IR interpretation [11,13]

22 O—H N—H C—H C—C HO-C=O C=_N C=O C=N C=C C=S N=O S=O C—N C—O benzene %T Graphical interpretation of functional groups in IR [2,10] B.K. SHARMA," Infrared spectroscopy”,spectroscopy,20 th edition, Goel publications, Delhi, print. 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2 nd edition,Narosa,Newdelhi, Chennai Print.  C-H OH, --NH 2, >NH,  C-H  C-H, Ar— C-H C—H, --COOH esters, alcohol, ethers, Nitro groups

23 Alkanes  C–H stretch from 3000–2850 cm -1  C–H bend or scissoring from cm -1  C–H rock, methyl from cm -1  C–H rock, methyl, seen only in long chain alkanes, from cm -1 Wave number cm C-H stretch C-H rock C-H scissoring Long chain CH 2 stretch Octane spectrum 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print. 23 General guidelines for IR interpretation [10,11]

24 Alkenes :-  C=C stretch from cm -1  =C–H stretch from cm -1  =C–H bend from cm % transmittance Wave number cm =C-H stretch C-H stretch –C-H stretch C=C str C-H sis C-H rock =C-H bond 1- Octene spectrum General guidelines for IR interpretation [1011] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

25 Alkynes :-  –C≡C– stretch from cm -1  –C≡C–H: C–H stretch from cm -1  –C≡C–H: C–H bend from cm C-H stretch C-H rock C-H scissoring C  C- H C  C- H C  C- C  C hexyne spectrum % transmittance Wavelength cm General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

26 Alkyl halides :-  C–H wag (-CH2X) from cm -1  C–X stretches (general) from cm -1  C– Cl stretch cm -1  C–Br stretch cm C-H stretch C-H wag C-H scissoring Long chain, C-Br stretch 1- bromo propane spectrum 26 General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

27 Aromatics:-  C–H stretch from cm -1  overtones, weak, from cm -1  C–C stretch (in-ring) from cm -1  C–C stretch (in-ring) from cm -1  C–H "loop" from cm -1 C-H stretch aromatics 3068 % transmittance 90 0 C-H stretch alkyl C- H stretch In aromatic ring Wavelength cm overtones In-plane C-H bending  Aromatic C-H stretches are left to 3000, and aliphatic C-H stretches are right to 3000 Spectrum of Toluene 27 General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

28 Alcohol:-  O–H stretch, hydrogen bonded cm -1  C–O stretch cm -1 (s)  The spectrum of ethanol is shown below. Note the very broad, strong band of the O–H stretch (3391) and the C–O stretches (1102, 1055). O-H stretch 3391 Wave number cm -1 % transmittance 90 0 C-H stretch C-O stretch Spectrum of Ethanol 28 General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

29 ketones  C=O stretch:  aliphatic ketones 1715 cm -1  α, β-unsaturated ketones cm -1  The spectrum of 2-butanone is shown below. This is a saturated ketone, and the C=O band appears at Note the C–H stretches (around 2991) of alkyl groups. C-H stretch C=O stretch Wave number cm -1 % transmittance butanone spectrum General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

30 Aldehydes:  H–C=O stretch cm -1  C=O stretch:  aliphatic Aldehydes cm -1  alpha, beta-unsaturated aldehydes cm -1  The spectra of benzaldehyde and butyraldehyde are shown below. Note that the O=C stretch of the alpha, beta-unsaturated compound -- benzaldehyde -- is at a lower wave number than that of the saturated butyraldehyde. C-H Stretch alkyl C=O stretch Wave number cm -1 % transmittance C-H aldehyde Benzaldehyde spectrum General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

31 Carboxylic acids :-  O–H stretch from cm- -1  C=O stretch from cm -1  C–O stretch from cm -1  O–H bend from and cm -1  The spectrum of hexanoic acid is shown below. Note the broad peak due to O–H stretch superimposed on the sharp band due to C–H stretch. Note the C=O stretch (1721), C–O stretch (1296), O–H bends (1419, 948), and C–O stretch (1296 O-H stretch and C-H stretch C=O stretch Wave number cm -1 % transmittance O-H band 1296 C-O stretch 948 O-H 31 General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

32 Esters :-  C=O stretch  aliphatic from cm -1  α, β-unsaturated from cm -1  C–O stretch from cm -1  The spectra of ethyl acetate and ethyl benzoate are shown below. Note that the C=O stretch of ethyl acetate (1752) is at a higher wavelength than that of the α, β-unsaturated ester ethyl benzoate (1726). Also note the C–O stretches in the region cm % transmittance Wave number cm Ethyl acetate C-H stretch C=O ester stretch C-O stretch C-O stretch 4 Ethyl benzoate C-H aromatic stretch C-H alkyl stretch C=O stretch , C-O stretch 32 General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

33 Amines :-  N–H stretch cm -1  1° amine: two bands from and cm -1  2° amine: one band from cm -1  3° amine: no bands in this region  N–H bend (primary amines only) from cm -1  C–N stretch (aromatic amines) from cm -1  C–N stretch (aliphatic amines) from 1250–1020 cm -1  N–H wag (primary and secondary amines only) from cm General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

34 90 % transmittance Wave number cm Aniline Shoulder band N-H primary amine C-N stretch Diethyl amine N-H stretch Secondary amine C-N stretching N-H waging 1 0, Tri ethyl amine C-N stretching 1 0,2 0,3 0 amine spectrums 34 General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

35 Nitro groups:-  N–O asymmetric stretch from cm -1  N–O symmetric stretch from cm -1 N-O stretch N-O stretch Wave number cm -1 % transmittance 90 0 N-O stretch Black spectrum Blue spectrum Nitro methane Meta nitro toluene 35 General guidelines for IR interpretation [10,11] 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 11.Dudles H,Williams,Ian Flemming,”infrared spectroscopy”, Spectroscopy Methods In Organic Chemistry, 5 th edition,Tata mecGrawHill.Education. Newyork, Singapore, Sydney, page no Print.

36 Example for interpretation of IR for known structure [9,10,14] Acetaminophen 14 (4-acetamido-Phenol) A.N-H Amide cm -1. B.Phenolic—OH cm cm -1 C.C—H Stretching cm -1. D.Aromatic overtone cm cm -1 E.>C=O Amide stretching cm -1 F.Aromatic C=C stretching cm -1. G.N-H Amide bending cm -1 H.Aromatic C=C stretching cm -1. I.>C—H bending cm -1 A B C D E F G H I 9. Robert M.Silverstien Francis X.Webster,”infrared spectroscopy”, spectroscopic identification of organic compounds, 6thedition, John Wiley, Chichester, Singapore, Toronto, Brisbane page no. 3.5, Print. 10. Jag Mohan,”infrared spectroscopy”, Organic Spectroscopy, Principles And Applications, 2ndedition,Narosa,Newdelhi, Chennai Print. 14.David watson,”infrared spectroscopy”, pharmaceutical Analysis, A test book for pharmacy students & pharmaceutical chemists, 2 nd edition, Elsevier churchil,livingston. Edinburgh,london,newyork,oxford,sydney, and Toronto. Print 36

37 15.www.cem.msu.edu. Web feb Examples for interpretation of IR for known structure 15 15

38 Tips for interpretation of IR for unknown structure 14  Always place relines to negative information evidence i.e., absence of band at 1900 cm cm absence of >C=O, >CHO  Always starts from higher frequency end of the spectrum.  Absence of band at 880 cm -1 —650 cm -1 indicates absence of aromatic ring.  For easy identification go for fingerprint and functional group region.  Finger print region range is 1400 cm cm -1. In this region if absorbance band is present the groups esters, alcohols, ethers, nitro are Confirmed.  Functional region range is 4000 cm cm -1.amines, alcohols, aromatic rings, carboxylic acids, alkynes, alkanes, alkenes, anhydrides, imides, etc, may be confirmed.  Stretching vibrations at 4000 cm cm -1.  Bending vibrations at 1500 cm cm David watson,”infrared spectroscopy”, pharmaceutical Analysis, A test book for pharmacy students & pharmaceutical chemists, 2 nd edition, Elsevier churchil,livingston. Edinburgh,london,newyork,oxford,sydney, and Toronto. Print

39 Sat’d C=0 C=C CH 3 CH 2 Aromatic P- Disubst Aromatic P- Disubst Carbonyl Group Carbon Oxygen Group Primary Amine Group Saturated Alkane Unsaturated Alkene / Aromatic Methyl Group Wave number cm -1 % transmittance NH 2 Unsat’d 39 Example for interpretation of IR for unknown structure [14,15] 15.www.cem.msu.edu. Web feb David watson,”infrared spectroscopy”, pharmaceutical Analysis, A test book for pharmacy students & pharmaceutical chemists, 2 nd edition, Elsevier churchil,livingston. Edinburgh,london,newyork,oxford,sydney, and Toronto. Print

40 OH stetching vibrational frequency CH aliphatic asymmetrical stretching vibrational band. The less intense band at 2860 – is the symmetrical stretching vibrational band CH2 characteristic absorption CO absorption 40 Example for interpretation of IR for unknown structure www.cem.msu.edu. Web feb POSITIONREDUCED MASS BOND STRENGTH (STIFFNESS) LIGHT ATOMS HIGH FREQUENCY STRONG BONDS HIGH FREQUENCY STRENGTHCHANGE IN ‘POLARITY’ STRONGLY POLAR BONDS GIVE INTENSE BANDS WIDTHHYDROGEN BONDING STRONG HYDROGEN BONDING GIVES BROAD BANDS Peak status Reason inference

41 Conclusion IR spectroscopy Drug discovery Drug Quality control Drug incompatibility On considering the all above aspects of “INFRA RED SPECTROSCOPY”. It is concluded that IR technique is “ an unbound spectroscopic technique for quality optimization from drug discovery to drug quality control parameters”. 41

42 THANK YOU 42 NOTE: This presentation does not include plagiarized material.


Download ppt "Name: Anil kumar Appapurapu College: Bapatla college of pharmacy, Bapatla. Year: M. Pharmacy, 2nd year. Profile link:"

Similar presentations


Ads by Google