The ir spectra in the region 4000–250 cm−1 in the solid state have been recorded for seventy-six 1,3-disubstituted 2-pyrazolin-5-ones in which 4-positions are coupled with various diazotized anilines. Correlations between structure and frequency are made. From the results obtained, a useful application of these spectral correlations can be derived for recognizing a pyrazolinone dye in an unknown compound by means of its spectrum. The strong bands at about 1650, 1550, 1340, 1260, and 1150 cm−1, and sometimes the strong or medium bands near 1000 and 680 cm−1 constitute a good indication of the presence of a 4-arylhydrazono pyrazolinone ring.
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References
1.
RandallH. M.FowlerR. G.FusonN., and DanglJ., Infrared Determination of Organic Compounds (D. Van Nostrand, Co., Inc., New York, 1949) p. 222.
2.
GagnonP. E.BoivinJ. L.McDonardR., and YaffeL., Can. J. Chem.32, 823 (1954).
3.
SuavelyF. A.TrahanovskyW. S., and SuydamF. H., J. Org. Chem.27, 994 (1961).
4.
YasudaH. and MidorikawaH., J. Org. Chem.31, 1722 (1966).
5.
JonesR.RyanA. J.SternhellS., and WrightS. E., Tetrahedron19, 1497 (1963).
6.
YasudaH. and MidorikawaH., Bull. Chem. Soc. Japan31, 1596 (1966).
7.
McDanielD. S. and BrownH. C., J. Org. Chem.23, 420 (1958).
8.
JonesB. N.ForbesW. F., and MuellerW. A., Can. J. Chem.35, 504 (1957).
9.
TodaS., Nippon Kagaku Zasshi80, 402 (1959).
10.
SuydamF. H., Anal. Chem.35, 193 (1963).
11.
ColthupN. B., J. Opt. Soc. Amer.40, 397 (1950).
12.
HadziD. and SkrbljakM., J. Chem. Soc.1957, 843 (1957).
13.
ThompsonH. W. and TempleE. B., Trans. Faraday Soc.41, 27 (1945).
14.
BakB.BrodersenS., and HansenL., Acta Chem. Scand.9, 749 (1955).
15.
KatritzkyA. R. and LagowskyJ. M., J. Chem. Soc.1959, 657 (1959).
16.
KatritzkyA. R. and BoultonA. J., Spectrochim. Acta17, 238 (1961).
17.
BorelloE. and ZecchinaA., Spectrochim. Acta19, 1703 (1963).
