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Infrared Spectrum of Bromochlorofluoromethane Earle K

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Infrared Spectrum of Bromochlorofluoromethane Earle K Journal of Research of the National Bureau of Standards Vol. 46, No. 5, May 1951 Research Paper 2208 Infrared Spectrum of Bromochlorofluoromethane Earle K. Plyler and Mary A. Lamb The spectrum of bromochlorofiuoromethane has been measured in order to compare the wave numbers of the fundamental bands with t hose of other substituted methanes con­ taining the halogens. The positions of the absorption bands have been determined for the liquid and vapor states and all fundamental bands except one at 220 cm- 1 have been observed. The position of this band has been predicted from other bands that are classified as com­ binations of two fundamental bands, one of which was the 220 cm - 1 band. Many of t he bands of low or medium intensity have been classified as combinations or overtones of the nine fundamentals. The spectra of many substituted me thanes have this Bureau, and the results showed that the dis­ been measured in the infrared, and normal coordinate tilled fraction with the intermediate boiling point, calculations have been made on the fundamental 37° C, was 98 percent of bromochlorofluoromethane. modes of vibration of these molecules. l Good agree­ The principal impurities were probably dichloro­ ment has been found between the experimental and bromomethane and dichlorofluoromethane. The theoretical values assigned to the fundamental fraction with the lower boiling point, 29.5° to 35.8° vibrations. C, showed 95.1 percent of bromochlorofluoro­ The number of different fundamental vibrations methane, and the most likely impurities were can be determined from the symmetry of the mole­ dibromofluoromethane, dichlorofluoromethane, and cule. For example, molecules like methane or tetra­ dichlorobromomethane. The spectra of the three fluoromethane have four different vibrations, mole­ fractions were essentially the same. Some slight cules of the type of chloroform and fluoroform have differences in the intensity of weak bands were noted; six different fundamental frequencies, and molecules these coincided in position with the strongest bands of the type of methylene chloride and bromochloro­ in the spectra of the most likely impurities and are f1uoromethane have nine separate fundamental fre­ attributed to those molecules. These are discussed quencies. When the hydrogens of methane are later. substituted by the different halogen atoms, the The infrared absorption spectrum of bromochloro­ number of molecular constants increases, and it is fluoromethane has been measured in both the liquid more difficult to obtain good agreement. between the and vapor states. Although all three distillation observed and calculated positions for the bands. fractions were measured, only the spectrum of the Methods for carrying out the calculations with some fraction with the intermediate boiling point, 37° C, simplifications have been described by Decius. 2 The will be presented since this was the fraction of highest compound bromochlorofluoromethane is of interest purity. In figure 1, A, is shown the region from 2 for it does not have a center or axis of symmetry. to 15 /1- of the spectrum of the compound in the liquid The purpose of this investigation was to study the state as measured by a Perkin-Elmer spectrometer spectrum of bromochlorofluoromethane and to assign with the lithium fluoride and sodium chloride prisms. the fundamental bands. A comparison of the spec­ The broken line portions of the curve represent the trum of bromochlorofluoroinethane with the assigned weak bands, which are probably due to the impuri­ vibrations in the spectra of related halogen­ ties present in the fraction, and they also represent substituted methanes is helpful in making the assign­ regions of atmospheric water absorption where the ments and in attributing them to motions of par­ shapes and positions of the bands were difficult to ticular atoms. The dichlorofluoromethane assign­ determine accurately. These regions have been ments are also helpful in making the identification plotted using the spectrum measured on a Baird of the C-Cl and C-F bending and stretching vibra­ infrared spectrophotometer. Five of the nine funda­ tions in bromochlorofluoromethane. The identifica­ mental vibrations are present in this region, and tion of the C-Br bending and stretching vibrations most of the other bands have been assigned as com­ were made by comparison of the spectrum with the bination or overtone bands. A list of the bands assigned spectrum of dibromochloromethane. with their assignments is included in table 1. The The bromochlorofluoromethane was obtained from region from 15 to 23 /1- , as measured with a potassium Halogen Chemicals Inc., where it was repurified so bromide prism, and the region from 23 to 38 /1-, as that it was suitable for spectroscopic measurements. measured with a thallium bromide-iodide prism, are The compound was redistilled into three fractions by shown in figure 1, B . Three of the remaining four W. Harold Smith, of the Bureau's Organic Chemistry fundamental bands have been assigned to bands in Section. Tests of the purity of two of the fractions this region. The ninth fundamental vibration has were made in the Mass Spectrometry Section of not been observed directly, but may be a value of 220 cm-1 on the basis of observed combination and 1 O. H erzberg, Infrared and Raman spectra of polyatomic molecules (D. Van difference bands. This band is beyond the range of Nostrand Co., Inc., New York, N. Y., 1945). ' J . C. D ecius. J. Chern. Phys. 16 , 214 (1948). the thallium bromide-iodide prism. 382 I l In figure 1, C, are shown the more intense bands in proximation the bands may be considered as arising the vapor spectrum in the region from 2 to 23 J1.. from stretching and bending vibrations of each Mo t of these bands show evidence of P , Q, and R peripheral atom (H, Br, Cl, F ) with respect to the branches. The C-H stretching vibration at 3,023 carbon atom. This would account for eight funda­ cm-1 i hown on an enlarged scale so that the detail mental modes of vibration. The ninth fundamental of the band can be seen more clearly. The bands band could be considered as a torsional motion of the shown are of the same relative intensities as they were molecule, but since the hydrogen atom i so much in the measurements of the liquid state. There is lighter tban the halogens, the motion in this mode noted, however, a slight shift to larger wave numbers may equally well be considered a second degree of of not more than 10 cm-1 for the vapor state from the freedom of bending of the CR bond. wave numbers observed in the liquid state spectrum. The spectrum of bromochlorofluoromethane should In table 1 are listed all of the observed bands as be similar to that of dichlorofluoromethane except observed in the liquid state of appreciable intensity for the modes of motion primarily involving with their intensities denoted by abbreviat,ions for the C-Br group, which should occur at lower fre­ very weak, weak, medium, strong, or very strong. quencies for bromochlorofluoromethane than the The assignments of the bands have also been given corresponding C-Cl group in dichlorofluoromethane. as fundamental, combination, overtone, or difference Thus, for example, the band with the wave number bands. All of the intense bands are classified and fall of 3,023 cm-1 is identified as the C-H stretching, into a consistent array based on the nine fundamental Pl, vibration and the bands with wave numbers of vibrations. Several of the assignments for weaker 1,202 and 1,299 cm-1 are classified as the two bending bands may not be correct, and eight observed weak vibrations of CH. These two types of vibrations bands have not been assigned in the table. It is are referred to as VCH and OCH, respectively, in table 1, possible that these weak bands arise from the small and the same type of symbols are used to designate quantities of impUTities in the compound. For the other bands. Similar relationships hold between example, the bands ob erved at 605, 721 , and 1,168 the unsymmetrical CHBrCIF and the other kindred cm-1 may be due to the dichlorobromomethane fun­ methane derivatives. damental frequencies V3, Jl7 , and Jl6 respectively, also A comparison of the fundamentals of all four re­ the observed band at 848 cm-1 may arise from tri­ lated molecules is shown in table 2. The assign­ chlorofluoromethane. The unassigned band at 790 ments of the observed bands of the three latter cm-1 possibly may be explained as a combination me thanes have been made and will be published later band of dichlorobromomethane, V3+ V5. To an ap- with a group of substituted methane derivatives. WAVE MUWIEItS 1M CN·I 3000 1000 . 1500 1100 1100 .00 000 700 t4 in C$z .......... 0.05111111 ~ 80 \\CS' ( ~ CHFCIBr ~ 60 '0 \ v;-- z /'--"'\ u ~ 20 \./ \ A o. 8 • WAVELUGTH IN M'CItONS " WAVE NUMBERS IN eM" '00 450 400 350 300 O.4mm CHFCIBr 080 ~ ~ 60 ~ l6mm " ,#'~ U ~zo B 0 ,. ,. 3' WAVELENGTH IN MICRON S 2200 ~o ~m PRESSURE \ ~4cm PRESSURE ~ 80 '0. cm V5<. CECe --"""""\ f.zemPRE SSURE ~ : Scm CELl. g60~ , , ~ 20 CHFCIBr VAPOR 0 C ' .20 3.25 :UO 3.35 4.5 5.0 7.0 7.5 8.0 0.5 9.5 10.0 WAVE LENGTH IN MICRON S FIGU RE 1. I nfraj'ed spectrum of bromochlorofluoromethane. A, Liquid state from 2 to 15 1'; B, liquid state from 14 to 38 1'; C, intellse bands, vapor statc from 3 to 161'. 383 TABLE 1. Classification of the observed bands The bands of bromofluorochloromethane have slightly of bromochlorofluoromethane smaller wave numbers than those of the correspond­ ing dichlorofluoromethane bands.
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