Analysis of the infrared spectra of some polydeuterated toluenes obtained by proton exchange with BF3-D3PO4 demonstrated the unreliability of this analytical tool in the 4000–900 cm−1 region. Useful correlations can be obtained in the 900–500 cm−1 region if suitable instrumentation is available. The previously unreported spectra of toluene-2,5-D, toluene-3,5-D and toluene-2,4, 6-D are described.
Get full access to this article
View all access options for this article.
References
1.
LampertP. and LecomteJ., Ann. Phys.18, 329 (1932).
2.
ColthupN., J. Opt. Soc. Am.40, 396 (1950).
3.
WhiffenD. H. and ThompsonH. W., J. Chem. Soc, 268 (1945).
4.
ColeA. R. H. and ThompsonH. W., Trans. Faraday Soc.46, 103 (1950).
5.
BellR. P.ThompsonH. W., and VagoE. E., Proc. Roy. Soc. (London)192A, 498 (1948).
6.
TiersG. V. D. and TiersJ. H., J. Chem. Phys.20, 761 (1952); TiersG. V. D., J. Chem. Phys.19, 1072 (1951).
7.
TurkevichJ.McKenzieH. A.FriedmanL., and SpurrR., J. Am. Chem. Soc.71, 4045 (1949).
8.
StevensonD. P. and WagnerC. D., J. Am. Chem. Soc.72, 5612 (1950); HonigR. E., Anal. Chem.22, 1474 (1950).
9.
BigelowL. A.JohnsonJ. R., and SandbornL. T., Org. Syn. Coll.3, 133 (1932); KornblumN., Org. Syn. Coll. Vol.3, 295 (1955).
10.
GoldV., and SatchellD. P. N., J. Chem. Soc, 3622 (1955); ibid., 2743 (1956); MackorE. L.SmitP. J., and Van Der WaalsJ. H., Trans. Faraday Soc53, 1309 (1957); LauerW. M.MatsonG. W., and StedmanG., J. Am. Chem. Soc.80, 6433 (1958); Ibid., 6437; and for a general review of electrophilic aromatic substitution see HineJ., Physical Organic Chemistry (McGraw—Hill Book Co., New York, 1962), p. 344–382.
11.
These synthesis will be described in detail, along with the kinetics results in the J. Org. Chem. (to be published).