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Mixed clusters of benzene derivatives and trihalogenmethanes have been prepared in a supersonic beam and studied with infrared vibrational predissociation spectroscopy detected by resonant two photon ionization (IR/R2PI).  We report the spectra of chloroform and fluoroform attached to the chromophores fluorobenzene, benzene, toluene,  p -xylene and their deuterated analogues. Instead of the typical H-bonding induced red-shift of the CH stretching frequency a blue-shift is observed. From a comparison with  ab initio  calculations, we propose sandwich-like structures bonded by a C–H...π hydrogen bond exhibiting an unusual partial charge transfer.

zeitschrift für physikalische chemie

Blue-Shift in the Frequencies of  the CH Stretches of Chloro- and Fluoroform Induced by C–H...π Hydrogen Bonding with Benzene Derivatives: the Influence of Electron Donating and Withdrawing Substituents