Non-covalent interactions
A hydrogen bond (H-bond), is a specific type of interaction that involves dipole-dipole attraction between a partially positive hydrogen atom and a highly electronegative, partially negative oxygen, nitrogen, sulfur, or fluorine atom (not covalently bound to said hydrogen atom). It is not a covalent bond, but instead is classified as a strong non-covalent interaction. It is responsible for why water is a liquid at room temperature and not a gas (given water's low molecular weight). Most commonly, the strength of hydrogen bonds lies between 0 - 4 kcal/mol, but can sometimes be as strong as 40 kcal/mol In solvents such as chloroform or carbontetrachloride one observes e.g. for the interaction between amides additive values of about 5 kJ/mol. According to L. Pauling the strength of a hydrogen bond is essentially determined by the electrostatic charges. Measurements of thousands complexes in chloroform or carbontetrachloride have led to additive free energy increments for all kind of donor-acceptor combinations.
Carbon–fluorine bond
The high electronegativity of fluorine (4.0 for F vs. 2.5 for carbon) gives the carbon–fluorine bond a significant polarity/dipole moment. The electron density is concentrated around the fluorine, leaving the carbon relatively electron poor. This introduces ionic character to the bond through partial charges (C—F). The partial charges on the fluorine and carbon are attractive, contributing to the unusual bond strength of the carbon–fluorine bond. The bond is labeled as "the strongest in organic chemistry," because fluorine forms the strongest single bond to carbon. Carbon–fluorine bonds can have a bond dissociation energy (BDE) of up to 544 kJ/mol. The BDE (strength of the bond) is higher than other carbon–halogen and carbon–hydrogen bonds. For example, the molecule represented by CHX has a BDE of 115 kcal/mol for carbon–fluorine while values of 104.9, 83.7, 72.1, and 57.6 kcal/mol represent carbon–X bonds to hydrogen, chlorine, bromine, and iodine, respectively.