Table 8.2 Detailed Table of Characteristic Infrared Absorption Frequencies

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1 Table 8.2 Detailed Table of Characteristic Infrared Absorption Frequencies The hydrogen stretch region ( cm 1 ). Absorption in this region is associated with the stretching vibration of hydrogen atoms bonded to carbon, oxygen, and nitrogen. Care should be exercised in interpreting very weak bands because these may be overtones of strong bands occurring at frequencies from cm 1, which is one-half the value of the weak absorption. Overtones of bands near 1650 cm 1 are particularly common Thomson Brooks/Cole, a part of The Thomson Corporation (1) O stretching 3600 cm 1 (sharp) unassociated O, 3400 cm 1 (broad) associated O ; Intensity: variable both bands frequently present in alcohol spectra; with strongly associated O (CO 2 or enolized ( -dicarbonyl compound), band is very broad (about 500 cm 1 with its center at cm 1 ). (2) N stretching 3400 cm 1 (sharp) unassociated N, 3200 cm 1 (broad) associated N ; Intensity: medium an N 2 group usually appears as a doublet (separation about 50 cm 1 ); the N of a secondary amine is often very weak. (3) 3300 C stretching of The complete absence of absorption in the region from cm 1 an alkyne indicates the absence of hydrogen atoms bonded to C==C or C C and usually signals the lack of unsaturation in the molecule. Because this absorption may be very weak in large molecules, care should be exercised in this interpretation. In addition to the absorption at about 3050 cm 1, aromatic compounds frequently show sharp bands of medium intensity at about 1500 and 1600 cm 1. (4) C stretching of an alkene Intensity: strong to medium (5) 3050 C stretching of an aromatic compound Intensity: variable; usually medium to weak (6) O strongly A very broad band in this region superimposed on the C stretching hydrogen-bonded frequencies is characteristic of carboxylic acids. Intensity: medium (7) C stretching of an As in previous C entries (3 5), complete absence of absorption in this aliphatic compound region indicates absence of hydrogen atoms bound to tetravalent carbon atoms. The tertiary C absorption is weak. (8) C stretching of Either one or two bands may be found in this region for a single aldehyde an aldehyde function in the molecule. Intensity: weak The triple-bond region ( cm 1 ). Absorption in this region is associated with the stretching vibration of triple bonds. (1) C N Nitriles conjugated with double bonds absorb at lower end of frequency range; nonconjugated nitriles appear at upper end of range. (2) C C This band is absent if the alkyne is symmetrical, and will be very weak in terminal alkynes, or absent if the alkyne is nearly symmetrical. variable in others.

2 The double-bond region ( cm 1 ). Absorption in this region is usually associated with the stretching vibration of carbon-carbon, carbon-oxygen, and carbon-nitrogen double bonds. (1) C O stretching of Carbonyls conjugated with double bonds absorb at lower end of range; an acid chloride nonconjugated carbonyls appear at upper end of range. (2) C O stretching of an Both bands are present; each band is altered by ring size and conjugation to and acid anhydride approximately the same extent noted for ketones. (3) C O stretching of an This band is subject to all the structural effects discussed for ketones; thus, a ester or lactone conjugated ester absorbs at about 1710 cm 1 and a -lactone absorbs at about Intensity: very strong 1780 cm 1. (4) C O stretching of an This value refers to carbonyl absorption frequency of acyclic, nonconjugated aldehyde or ketone aldehyde or ketone having no electronegative groups, for example halogens, Intensity: very strong near the carbonyl group; because this frequency is altered in a predictable way by structural alterations, the following generalizations are valid: (a) Effect of conjugation: Conjugation of carbonyl group with an aryl ring or carbon-carbon double or triple bond lowers the frequency by about 30 cm 1. If the carbonyl group is part of cross-conjugated system (unsaturation on each side of the carbonyl group), the frequency is lowered by about 50 cm 1. (b) Effect of ring size: Carbonyl groups in six membered and larger rings exhibit approximately the same absorption as acyclic ketones; carbonyl groups in rings smaller than six absorb at higher frequencies: for example, a cyclopentanone absorbs at about 1745 cm 1 and a cyclobutanone at about 1780 cm 1. The effects of conjugation and ring size are additive: A 2-cyclopentenone absorbs at about 1710 cm 1, for example. (c) Effect of electronegative atoms: An electronegative atom, especially oxygen or halogen, bound to the -carbon atom of an aldehyde or ketone usually raises the position of the carbonyl absorption frequency by about 20 cm 1. (5) 1700 C O stretching Conjugation lowers this absorption frequency by about 20 cm 1. of an acid of (6) C O stretching of an Conjugation lowers the frequency of this band by about 20 cm 1. The amide or lactam frequency of the band is raised about 35 cm 1 in ( -lactams and 70 cm 1 in -lactams. (7) C C stretching Conjugated alkenes appear at lower end of range, and absorptions are of an alkene medium to strong; nonconjugated alkenes appear at upper end of range, and Intensity: variable absorptions are usually weak. The absorption frequencies of these bands are raised by ring strain but to a lesser extent than noted with carbonyl functions. (8) C N stretching This band is usually weak and difficult to assign. Intensity: variable

3 The hydrogen bending region ( cm 1 ). Absorption in this region is commonly due to bending vibrations of hydrogen atoms attached to carbon and to nitrogen. These bands generally do not provide much useful structural information. In the listing, the bands that are most useful for structural assignment are marked with an asterisk. (1) 1600 N 2 bending Intensity: In conjunction with bands in the 3300 cm 1 region, this band is often used to strong to medium characterize primary amines and amides. (2) 1540 N bending Intensity: In conjunction with bands in the 3300 cm 1 region, this band is used to generally weak characterize secondary amines and amides. This band, like the N stretching band in the 3300 cm 1 region, may be very weak in secondary amines. (3)* 1520 and 1350 N 2 coupled stretching This pair of bands is usually very intense. bands (4) 1465 C 2 bending Intensity of this band varies according to the number of methylene groups Intensity: variable present; the more such groups, the more intense the absorption. (5) 1410 C 2 bending of This absorption is characteristic of methylene groups adjacent to carbonyl carbonyl containing functions; its intensity depends on the number of such groups present in the component molecule. Intensity: variable (6)* 1450 C 3 The band of lower frequency (1375 cm 1 ) is usually used to characterize a and 1375 methyl group. If two methyl groups are bound to one carbon atom, a characteristic doublet (1385 and 1365 cm 1 ) is observed. (7) 1325 C bending Intensity: weak This band is weak and often unreliable Thomson Brooks/Cole, a part of The Thomson Corporation The fingerprint region ( cm 1 ). The fingerprint region of the spectrum is generally rich in detail and contains many bands. This region is particularly diagnostic for determining whether an unknown substance is identical to a known substance, the IR spectrum of which is available. It is not practical to make assignments to all these bands because many of them represent combinations of vibrational modes and therefore are very sensitive to the overall molecular structure; moreover, many single-bond stretching vibrations and a variety of bending vibrations also appear in this region. Suggested structural assignments in this region must be regarded as tentative and are generally taken as corroborative evidence in conjunction with assignments of bands at higher frequencies. (1) 1200 It is not certain whether these strong bands arise from C O bending or C O O stretching vibrations. One or more strong bands are found in this region in the spectra of alcohols, ethers, and esters. The relationship indicated between structure and band location is only approximate, and any structural assignment based on this relationship must be regarded as tentative. Esters often exhibit one or two strong bands between 1170 and 1270 cm 1. (2) 1150 (3) 1100 C O C O

4 (4) 1050 C 2 O This pair of strong bands characterizes a terminal vinyl group. (5) 985 and 910 This strong band is present in the spectra of trans-1,2-disubstituted ethylenes. C bending (6) 965 This strong band characterizes a 1,1-disubstituted ethylene group and its frequency may be increased by cm 1 if the methylene group is bound to an electronegative group or atom. C bending (7) Very unreliable; this band is not always present and frequently seems to be outside this range because substituents are varied. C bending (8) This band, attributable to a cis-1,2-disubstituted ethylene, is unreliable because it is frequently obscured by solvent absorption or other bands. (9) 700 These bands are of limited value because they are frequently obscured by solvent absorption or other bands. They are most useful when independent Intensity: variable evidence leads to a structural assignment that is complete except for positioning of aromatic substituents. (10) 750 and 690 (11) 750 (12) 780 and 700 C bending C bending Intensity: very strong and 1,2,3- Intensity: very strong

5 (13) 825 and 1, 2, 4- Intensity: very strong (14) C F The position of these bands is quite sensitive to structure. As a result, they are not particularly useful because the presence of halogen is more easily detected by chemical methods. The bands are usually strong. (15) C Cl (16) C Br (17) C I

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