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Author(s)
Gas chromatographic measurements of the retention
times of alkyl naphthalenes on packed columns with polar and non-polar
stationary phases have proven that the logarithm of the relative
retention time increases bi-linearly (not linearly) with the number of
carbon atoms in a molecule. This is caused by a strong inclination of
alkyl side chains toward intramolecular cyclization. A FTIR spectral
analysis has shown that longer alkyl side chains of alkyl naphthalenes
are cyclized through an interaction between the terminal CH3
group and the aromatic ring. Conventional aromatic-aliphatic molecules
thus become new molecules with quasi-alicyclic rings. This, however,
alters the effect of non-covalent van der Waals attractive forces both
inside and outside the molecules, which is reflected in an exponential
increase of the retention times of alkyl naphthalenes with a side chain
longer than propyl and in the bi-linearity of the logarithmic dependence
of the relative retention times on the number of carbons in the
molecule.
Cite this paper
Straka, P. , Novotná, M. , Buryan, P. and Bičáková,
O. (2014) The Cyclization of Alkyl Side Chains of Naphthalenes: The
GC/Potential Energies/FTIR Approach. American Journal of Analytical Chemistry, 5, 957-968. doi: 10.4236/ajac.2014.514103.
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