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2 ! = 1 2"c k (m + M) m M wavenumbers! =!/c = 1/" wavelength frequency! units: cm 1 for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency of the vibration in different compounds, the same type of functional group absorb in the same region of the I Factors that determine! 1. Mass: larger mass = lower frequency (longer wavelength)

3 Factors that determine! 2. Bond strength (k) Stronger bonds (tighter springs) vibrate with higher frequency 3. Type of vibration Stretching (along the line of the chemical bond) Vs Bending (out of line with the chemical bond) For the same bond, stretch is higher energy (i.e. higher frequency) To see molecules in I, transition must result in a dipole change I active I stretch essentially absent I stretch essentially absent

4 Coupled interactions occur when! 1) vibrations of bonds related by symmetry! 2) common atoms between groups! 3) independent groups absorb at same frequency Commonly observed for C 2 groups Stretches symmetrical unsymmetrical Bends in plane rock (symmetrical) scissor (unsymmetrical)

5 N-Alkanes interpreted in terms of 4 vibrations:! - stretching and bending of C and C C bonds!! C C bends: ca. 500 cm 1 (out of spectral window)!! C C stretches: cm 1, weak bands!!! not of value for interpretation (fingerprint)!!!! more characteristic!! C stretches: occurs from cm 1!!! C 3 :! 2962 cm 1, asymmetrical stretch!!!! 2872 cm 1, symmetrical stretch!!! C 2 :! 2926 cm 1, asymmetrical stretch!!!! 2853 cm 1, symmetrical stretch!!!! Note precision!!! n-alkanes C- Stretches! C 2 (s) 1467 cm 1 scissor C 3 (s) 1375 cm 1 C 3 (as) 1450 cm 1 C 2 (s) 720 cm 1 ock Alkanes of 7 or more carbons C 3 (as) 2964 cm 1 C 2 (as) 2924 cm 1 C 3 (s) 2872 cm 1 C 2 (s) 2853 cm 1 C- Bends C 12 25

6 Fingerprinting C Similar But Not Identical C Unconjugated Alkenes linear alkenes: - C=C stretch: moderate to weak absorption at cm 1!!! 1640 cm 1, moderate 1650 cm 1, moderate weak moderate 1670 cm 1 weak C=C : - stretch: " 3000 cm 1

7 Unconjugated Alkenes C- stretch 3049 cm 1 vertone of 910 cm -1 Absorption (1820 cm 1 ) C=C stretch 1642 cm 1 C 2 rock 720 cm 1 ut of plane C=C bends 991, 910 cm 1 1-decene I tutor

8 cyclic alkenes: - C=C stretch: sensitive to ring strain C cm cm cm cm cm cm 1 cumulated alkenes: - C=C=C stretch (asymmetric): cm 1 conjugated alkenes: -the alkene bond stretching vibrations in alkenes w/o a center of symmetry give rise to two C=C stretches! -for symmetrical molecules, e.g. butadiene, only the asymmetric! stretch is observed Me 1650 cm 1 (as) 1600 cm 1 (s) 1600 cm 1 (as) Conjugated Double Bonds C- stretch 3090 cm 1 Symmetrical C=C stretch 1640 cm 1 (weak) Asymmetrical C=C stretch 1598 cm 1 (strong) ut of plane C=C bends 990, 892 cm 1

9 Alkynes C C stretch: weak absorption at cm 1 - not observed for symmetrical alkynes (v. weak for pseudo symmetric alkynes - terminal alkynes (-C C-) absorptions are stronger than internal (-C C-) absorptions!!!! C C stretch: cm 1 - strong, narrow (as compared to or N) C C bend: cm 1 : broad, strong absorption cm 1, overtone of above Terminal Alkynes Alkyne CC stretch 2119 cm 1 Alkyne C- bend overtone 1260 cm 1 Alkyne C- stretch 3310 cm 1 Alkyne C- bend 630 cm 1

10 Mononuclear Aromatic ydrocarbons (benzene) ut of plane bending of aromatic C- bonds: most informative cm 1 - intense bands, strongly coupled to adjacent hydrogens on the ring - position and number of bands gives information about the substitution pattern (particularly useful for alkyl substituted aromatics. Substitution of polar groups can give rise to exceptions)!!! C=C stretch: cm 1 C C stretch: ; cm 1 C C out of plane ring bending: cm 1 Mononuclear Aromatics vertone bands cm 1 Aromatic C- Stretches 3087, 3062, 3026 cm 1 Aromatic C-C Stretches ; cm 1 Aromatic C- in plane bends cm 1 out of plane ring bending 428 cm 1 Aromatic C- out of Plane bends 728 cm cm -1

11 C 3 C 3 C 3 C cm -1 C 3 C cm cm cm - Alcohols and Phenols Strongly dependent on hydrogen-bonding - non-hydrogen bonded groups absorb strongly in the cm 1 range. vapor phase; dilute, non polar solvent; very hindered not -bonded even when 'neat' too hindered Intermolecular hydrogen bonding occurs as conc. increases; - accompanied by a shift to lower freq. ( cm 1 ), at the expense of the free band - Pronounced for intramolecular -bonding C 3 C cm 1 in dilute CCl cm 1 neat 3077cm 1 in dilute CCl 4 regardless of concentration

12 C stretching Vibrations Alcohols ( cm 1)!! Phenols ( cm 1 ) primary alcohol: cm -1 secondary alcohol: tertiary alcohol: cm cm cm cm 1 Ethers C C stretching bands are most characteristic bands - strong because of strong dipole moment aliphatic ethers: strong band due to asymmetrical stretching,! cm 1 (usually 1125 cm 1 )!! weak band due to symmetrical stretching (lower freq) Alkyl aryl ethers: asymmetrical stretch at cm -1!! symmetrical stretch at cm 1 Vinyl alkyl ethers: asymmetrical stretch at cm -1!! symmetrical stretch at cm 1!! + _

13 Carbonyls C= stretch easily recognized, intense band Ketones, aldehydes, acids, esters, lactones, acid halides, anhydrides, amides and lactams all show C= stretching in the region cm 1. Position is determined by (1) physical state (2) electronic and mass of neighboring groups (3) conjugation (4) hydrogen bonding (5) ring strain Ketones aliphatic: normal position of a neat aliphatic ketone is 1715 cm 1 competing effects G inductive: increases! F Cl Br (monomer) G + resonance: decreases! N S

14 Ketones conjugation: shifts position to lower frequency alkene or phenyl group causes absorption in the cm 1 region. For!,"-unsaturated carbonyls, 2 absorptions may be observed C cm cm -1 vertone of C= stretch 1685 cm -1 For!,"-unsaturated carbonyls, 2 absorptions may be observed C 3 C 3 s-trans 1685 cm 1 s-cis 1699 cm 1 1,3-Diketones keto enol cm 1 hydrogen bonding broadens and shifts the carbonyl absorption to shorter! stretching 3 C C cm cm -1 3 C C 3

15 Cyclic Ketones The bond angle influences the absorption frequency of the C= C! C In strained rings, interaction with the adjacent C-C bonds increases the frequency of C= stretching 1715 cm cm cm 1 Aldehydes C= stretch Aliphatic aldehydes: C= stretch at cm 1 Electron withdrawing groups shift to higher frequency Conjugative groups shift to lower frequency ( cm 1 ) 3 C Cl 3 C 1730 cm cm cm cm cm 1 C stretch cm 1 ften, two bands are observed (the other is a result of an overtone of the C bend of the aldehyde)

16 Carboxylic Acids stretch free (ca cm -1 ) is observed only in the vapor phase or in very dilute (<0.01 M) solution in a non-polar solvent therwise, acids exist as dimers Intense, stretching in the cm 1 region centered near 3000 cm 1 C= stretch monomer: 1760 cm 1 for aliphatic acids dimer: ydrogen bonding reduces the frequency of the asymmetric C= stretch, especially when intramolecular alkyl cm -1 alkyl aryl cm -1 aryl 1665 cm -1 Esters C= stretch saturated aliphatic esters: C=: cm 1 formates,!,"-unsaturated, and benzoate esters: cm 1 phenyl or vinyl esters: cm 1 C stretches (strong absorptions; asymmetrical coupled vibrations) saturated aliphatic esters (except acetates): C : cm 1 acetates: 1240 cm 1!,"-unsaturated esters: cm 1 benzoate esters: cm 1

17 C 2 C cm 1 C= 1243 cm 1 C 1763 cm 1 C= 1199, 1164, 1145 cm 1 C 1730 cm 1 C= 1770 cm 1 C= 3 C 1823 cm 1 C=

18 Acid alides Cl cm 1 Cl cm 1 Anhydrides Two carbonyl stretches (symmetrical and asymmetrical) alkyl alkyl 1818; 1750 cm ; 1720 cm ; 1782 cm 1 Amides N stretching: N 2 N Two bands 3520 (as), 3400 (s) cm 1 (dilute) 3350 (as), 3180 (s) cm 1 (conc) cm 1 (dilute) C= stretching (Amide I band): N (s) cm 1, multiple bands due to -bonding (conc) 1690 cm 1 (dilute) 1650 cm 1 (conc) (except C 3 CN 2, which absorbs at 1694 cm 1 ) N N cm 1 (dilute) 1640 cm 1 (conc) cm 1 (-bonding not possible, unless in protic solvent)

19 Amides N Bending (Amide II band): N cm 1 (dilute)- separate from amide I cm 1 (conc)- overlap with the amide I band N cm 1 (dilute) (s) cm 1 (conc) Lactams N N N 1650 cm cm cm 1 Secondary lactams do not have an N bending band (Amide band II) near 1550 cm -1. This is a Characteristic of s-trans lactams.

20 Et EtN N 1662 (II) 1662 cm -1 (I) 3 C N C cm -1 (I) 1565 cm-1 (II) Amines N stretching - in dilute solution, primary amines (N 2 ) display 2 bands, near 3500 and 3400 cm 1. These represent free asymmetrical and symmetrical stretches. - in dilute soln, secondary amines ( 2 N) display one band near cm 1. - weaker and sharper than - neat primary aliphatic amines (alkyln 2 ) absorb at and cm -1. ArylN 2 absorb at slightly higher frequencies.

21 Nitriles alkyl C N C N cm cm 1 Nitro compounds 2 bands from the asymmetrical and symmetrical stretching of the N bond alkyln 2 N cm -1 and 1372 cm cm -1 and cm (as) 1347 (s)

22 Vinyl alkyl ethers: C=C stretch at cm -1 often a doublet!! + _ + _ trans: ~1620 cm 1 cis: ~1640 cm 1 vinyl ethers- wagging shifted to lower frequency alkyl terminal wag: 813 cm 1 terminal wag: 909 cm 1 trans C wag: 960 cm -1 trans C wag: 1000 cm -1 Amines N stretching - in dilute solution, primary amines (N 2 ) display 2 bands, near 3500 and 3400 cm 1. These represent free asymmetrical and symmetrical stretches. - in dilute soln, secondary amines ( 2 N) display one band near cm 1. - weaker and sharper than - neat primary aliphatic amines (alkyln 2 ) absorb at and cm -1. ArylN 2 absorb at slightly higher frequencies.

23 N is in similar region to but looks very different!

24

25 Infrared spectra: It is important to remember that the absence of an absorption band can often provide more information about the structure of a compound than the presence of a band. Be careful to avoid focusing on selected absorption bands and overlooking others. Use the examples linked to the table to see the profile and intensity of bands. emember that the absence of a band may provide more information than the presence of an absorption band. Look for absorption bands in decreasing order of importance: 1.the C- absorption(s) between 3100 and 2850 cm-1. An absorption above 3000 cm-1 indicates C=C, either alkene or aromatic. Confirm the aromatic ring by finding peaks at 1600 and 1500 cm-1 and C- out-of-plane bending to give substitution patterns below 900 cm-1. Confirm alkenes with an absorption generally at cm-1. C- absorption between 3000 and 2850 cm-1 is due to aliphatic hydrogens. 2.the carbonyl (C=) absorption between cm-1; this strong band indicates either an aldehyde, ketone, carboxylic acid, ester, amide, anhydride or acyl halide. The an aldehyde may be confirmed with C- absorption from 2840 to 2720 cm-1. 3.the - or N- absorption between 3200 and 3600 cm-1. This indicates either an alcohol, N- containing amine or amide, or carboxylic acid. For -N2 a doublet will be observed. 4.the C- absorption between 1080 and 1300 cm-1. These peaks are normally rounded like the - and N- peak in 3. and are prominent. Carboxylic acids, esters, ethers, alcohols and anhydrides all containing this peak. 5.the CC and CN triple bond absorptions at cm-1 are small but exposed. 6.a methyl group may be identified with C- absorption at 1380 cm-1. This band is split into a doublet for isopropyl(gem-dimethyl) groups. 7.structure of aromatic compounds may also be confirmed from the pattern of the weak overtone and combination tone bands found from 2000 to 1600 cm-1.

26 C Ketones aliphatic: normal position of a neat aliphatic ketone is 1715 cm 1 conjugation: shifts position to lower frequency alkene or phenyl group causes absorption in the cm 1 region. For!,"-unsaturated carbonyls, 2 absorptions may be observed C cm cm -1 vertone of C= stretch 1685 cm -1 For!,"-unsaturated carbonyls, 2 absorptions may be observed C 3 C 3 s-trans 1685 cm 1 s-cis 1699 cm 1

27 C Mononuclear Aromatic ydrocarbons (benzene) ut of plane bending of aromatic C- bonds: most informative cm 1 - intense bands, strongly coupled to adjacent hydrogens on the ring - position and number of bands gives information about the substitution pattern (particularly useful for alkyl substituted aromatics. Substitution of polar groups can give rise to exceptions)!!! C=C stretch: cm 1 C C stretch: ; cm 1 C C out of plane ring bending: cm 1

28 Mononuclear Aromatics vertone bands cm 1 Aromatic C- Stretches 3087, 3062, 3026 cm 1 Aromatic C-C Stretches ; cm 1 Aromatic C- in plane bends cm 1 out of plane ring bending 428 cm 1 Aromatic C- out of Plane bends 728 cm cm -1 C

29 Alcohols and Phenols Strongly dependent on hydrogen-bonding - non-hydrogen bonded groups absorb strongly in the cm 1 range. vapor phase; dilute, non polar solvent; very hindered Intermolecular hydrogen bonding occurs as conc. increases; - accompanied by a shift to lower freq. ( cm 1 ), at the expense of the free band - typically at 3300 cm 1 - Pronounced for intramolecular -bonding C stretching Vibrations Alcohols ( cm 1)!! Phenols ( cm 1 ) primary alcohol: cm -1 secondary alcohol: tertiary alcohol: cm -1 C 8 7 N

30 Nitriles alkyl C N C N cm cm 1 C ,

31 Aldehydes C= stretch 3 C Cl 3 C 1730 cm cm cm cm cm 1 C stretch cm 1 ften, two bands are observed (the other is a result of an overtone of the C bend of the aldehyde) C37N

32 Amides N stretching: N 2 Two bands 3520 (as), 3400 (s) cm 1 (dilute) 3350 (as), 3180 (s) cm 1 (conc) N cm 1 (dilute) (s) cm 1, multiple bands due to -bonding (conc) C= stretching (Amide I band): N 2 N N cm 1 (dilute) 1650 cm 1 (conc) (except C 3 CN 2, which absorbs at 1694 cm 1 ) cm 1 (dilute) 1640 cm 1 (conc) cm 1 (-bonding not possible, unless in protic solvent) N Bending (Amide II band): N N cm 1 (dilute)- separate from amide I cm 1 (conc)- overlap with the amide I band cm 1 (dilute) (s) cm 1 (conc) C

33 Esters C= stretch saturated aliphatic esters: C=: cm 1 formates,!,"-unsaturated, and benzoate esters: cm 1 phenyl or vinyl esters: cm 1 C stretches (strong absorptions; asymmetrical coupled vibrations) saturated aliphatic esters (except acetates): C : cm 1 acetates: 1240 cm 1!,"-unsaturated esters: cm 1 benzoate esters: cm 1 C 7 5 Cl ,

34 Acid alides Cl Cl cm cm 1

35 70

36 71

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