We investigate a wide range of hydrogen bonded complexes using density functional theory level of theory with aug-cc-pvtz basis set and natural bond orbital. For each complex (B"¦HA), we obtain a variety of experimentally measurable descriptors: IR frequency shift of the hydride bond, H-bond penetration distance, covalent bond length shift and NMR proton shielding shift. We also evaluate theoretical descriptors that are related to inter-molecular B"¦HA †” BH+"¦A- resonance covalency: charge transfer, and H-bond order and covalent bond order. Correlation coefficients are evaluated to relate each descriptor to the principle property hydrogen bond energy as well as to one another.