Think like a database: Substructure searching in the classroom

CINF 37

Judith N. Currano, currano@pobox.upenn.edu, Chemistry Library, University of Pennsylvania, 3301 Spruce St. 5th Floor, Philadelphia, PA 19104
Substructure searching is critical in many areas of chemistry, including in synthetic organic chemistry because, when trying to synthesize novel compounds, exact structure searches will not retrieve the information needed to construct the molecule. However, this search technique is frequently difficult for students to grasp; it requires them to think like databases instead of chemists. The author presents several techniques and methods of teaching substructure searching at various levels, based on the following points: what a substructure is and what it can do; the circumstances under which this type of search should be employed; how one should analyze a molecule to create a set of specifications for a substructure; and where and how one can actually run a substructure search. The teaching of substructure searching in both undergraduate and graduate courses is discussed, and suggestions for contexts in which to present the material are made.