Does fluoromethane form a hydrogen bond with water?

Fluorinated organic compounds have become increasingly important in the pharmaceutical and agricultural industries. However, even the simplest aspects of these compounds are still not well understood. For instance, it is an open question as to whether fluoroorganics can form a hydrogen bond. To answer this question, this work compares the complex CH(3)F···HOH with 10 other complexes including the water dimer, the water-ammonia dimer, the methane-water dimer, and the methane dimer, among others. The features that are compared include binding energy and its electrostatic and dispersive components, geometry, vibrational frequencies, charge transfer, and topological analysis of the electron density. All of these are consistent with a hydrogen bond forming in CH(3)F···HOH. Moreover, all features of this dimer appear to be quite similar in kind, although slightly lesser in degree, than the corresponding features of the water dimer.