Nineteen quantitative relationships are presented which enable the calculation of certain CH wag group frequencies in some substituted benzenes, naphthalenes, and acetylenes. Four involve computer calculation of molecular orbital electron densities and one involves Hammett values. The remaining 14 relationships involve simple functions between different CH wag group frequencies based on electron density relationships. This verifies a general tendency for unsaturated CH wag force constants to be weakened when the total electron density on the carbon of the CH is increased.
ColthupN. B. and OrloffM. K., Spectrochim. Acta27A, 1299 (1971).
2.
KrossR. D.FasselV. A., and MargoshesM., J. Am. Chem. Soc.78, 1332 (1956).
3.
PopleJ. A.SantryD. P., and SegalG. A., J. Chem. Phys.43, S129 (1965); PopleJ. A. and SegalG. A., J. Chem. Phys.43, S136 (1965), 44, 3289 (1966).
4.
PopleJ. A. and GordonM., J. Am. Chem. Soc.89, 4253 (1967).
5.
KingG. W. and MouleD., Spectrochim. Acta17, 286 (1961).
6.
BellE. E. and NielsenH. H., J. Chem. Phys.18, 1382 (1950).
7.
TurrelG. C.JohnsW. D., and MakiA. J., J. Chem. Phys.26, 1544 (1957).
8.
NyquistR. A. and PottsW. J., Spectrochim. Acta16, 419 (1960).
9.
SheppardN., J. Chem. Phys.17, 455 (1949).
10.
JonesA. V., Proc. Roy. Soc. (London)A211, 285 (1952).
11.
SheppardN., J. Chem. Phys.17, 74 (1949).
12.
BentlyF. F.SmithsonL. D., and RozekA. L., Infrared Spectra and Characteristic Frequencies 700–300 cm−1 (Interscience Publishers, New York, 1968), Chap. 2, p. 24.
13.
RichardsonW. S. and GoldsteinJ. H., J. Chem. Phys.18, 1314 (1950).
14.
WhiffenD. H., Spectrochim. Acta7, 253 (1955).
15.
SchmidE. W.BrandmullerJ., and NonnenmacherG., Z. Electrochem.64, 726, 940 (1960).
16.
VarsanyiG., Vibrational Spectra of Benzene Derivatives (Academic Press, New York, 1969), Chap. 3, p. 336.
17.
Documentation of Molecular Spectroscopy (Butterworth and Company, Ltd., London, 1970).
18.
American Petroleum Institute Research Project 44 (Carnegie Institute of Technology, Pittsburgh, 1959).
19.
PouchertC. J., The Aldrich Library of Infrared Spectra (Aldrich Chemical Company, Incorporated, Milwaukee, 1970).
20.
PottsW. J. and NyquistR. A., Spectrochim. Acta15, 679 (1959).
21.
ExnerO., Advances in Linear Free Energy Relationships, ChapmanN. B. and ShorterJ., Eds. (Plenum Press, New York, 1972), Chap 1, p. 28.
22.
HuisgenR. and ZirngiblL., Chem. Ber.91, 2375 (1958).