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A structural and spectroscopic investigation of the hydrochlorination of 4-benzylaniline: the interaction of anhydrous hydrogen chloride with chlorobenzene

Author(s): E. K. Gibson, J. M. Winfield, K. W. Muir, R. H. Carr, A. Eaglesham, A. Gavezzotti, S. F. Parker, D. Lennon

The hydrochlorination of 4-benzylaniline in chlorobenzene to produce 4-benzylaniline hydrochloride has been examined. This has required spectroscopic and computational analysis of the solvation of gaseous HCl in the process solvent. The characterisation of the reagent and product of the hydrochlorination reaction by various techniques, including FTIR and H-1 NMR spectroscopy and X-ray diffraction, is described. The infrared spectrum of the hydrochloride salt contains a strong Fermi resonance interaction, readily distinguishing it from that of the starting material. Using the structural results as a basis, the lattice energies of reagent and product have been evaluated by the recently developed PIXEL method. This method allows the contributions of specific intermolecular interactions to the total lattice energy to be assessed and, in this case, tentatively correlated with solubility measurements.

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ISBN: 1463-9076
Publication Year: 2009
Periodical: Physical Chemistry Chemical Physics
Periodical Number: 2
Volume: 11
Pages: 288-297
Author Address: