Effect of Ring Size on the Infrared Spectra of Cyclic Ethers. Characteristic Frequencies of Trimethylene Oxides and Tetrahydrofurans

  • Barrow G
  • Searles S
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RECEIVED JULY 25, 1952 The infrared spectra of several trimethylene oxides and tetrahydrofurans have been obtained. These rings are charac-The trimethylene oxides also show consistently It is also shown that these strong infrared bands fit in regularly with similar bands of the 3-and It is shown that this series of infrared bands arises from an antisymmetric type vibration of the ether The terized by very strong bands at 10.2 to 10.3 and 9.1 to 9.3 strong bands at 8 microns. 6-membered rings. links and that corresponding vibrations of the cyclic hydrocarbons give rise to frequencies which form a similar series. strong polarized Raman bands of these series are also added for comparison. respectively. The infrared spectra of the cyclic ethers have not been studied sufficiently to allow the assignment of infrared bands for the general identification of these compounds. Although a number of ethylene oxides have been studied,' the trimethylene oxides have not been investigated in the infrared and the infrared spectra of only the unsubstituted tetra-hydrofuran and tetrahydropyran are available. ls2 It seemed of interest to measure the infrared spectra of several trimethylene oxides and tetrahydrofurans available in this Laboratory and to consider possible assignments of the bands observed. A correlation of some of the Raman bands of 3-, 4-, 5-and 6-membered rings, including the ethers, has been discussed by Kohlrausch and Reitz3 but no similar attempt has been made in the infrared. Another purpose of this work was to compare the effect of ring size on certain infrared active ring vibrations with that observed by Kohl-rausch and Reitz in the Raman spectra.

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  • Gordon M. Barrow

  • Scott Searles

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