Statistical descriptors to measure the effectiveness of hydrogen bonding groups and an example of ether oxygenElectronic supplementary information (ESI) available. ESI contains data for different types of HB groups. See DOI: 10.1039/c1ce05034f.

To quantify the effectiveness of hydrogen-bonding donors and acceptors for forming interactions, we here introduce the concept of statistical competitiveness, defined in terms of three numerical parameters namely, absolute, relative and exclusive statistical competitiveness. The concept can be applied to evaluate the effectiveness of a donor or acceptor in any chemical context. We have evaluated the efficacy of ether oxygen for hydrogen-bonding with respect to carbonyl oxygen and nitrogen acceptors. The quantification in terms of statistical parameters reveals a striking result that the population of hydrogen-bonding groups predominately dictates their effectiveness irrespective of their acidic or basic strengths. The quantification of the competitiveness serves to estimate better the outcome of crystal structure prediction and engineering methodologies, and molecular docking. [ABSTRACT FROM AUTHOR]