M.C. Etter, "Encoding and decoding hydrogen-bond patterns of organic compounds," Accounts of Chemical Research, 23:120-26, 1990.
Margaret C. Etter (University of Minnesota, Minneapolis): "Despite hydrogen bonds' role as an essential component of life processes, there is an unspoken ethic that hydrogen-bond patterns are not predictable. In this paper, a new perspective on hydrogen bonds, based on analyses of small-molecule organic-crystal structures, is presented that challenges this assumption. A method for deconvoluting complex hydrogen-bond patterns into independent and predictable components from the common organic functional groups is described.
"Hydrogen-bond rules are derived by `decoding' hundreds of organic crystal structures using the graph theoretical approach. These rules are then applied in an `encoding' process, whereby hydrogen-bond patterns of new types of molecules, and of host/guest interactions, are predicted. This qualitative method is shown to be useful in designing new materials, in predicting selectivity in molecular recognition processes, and in demonstrating that scientists...