We describe and evaluate experimentally a method for clustering words according to their dis- tribution in particular syntactic contexts. Words are represented by the relative frequency distributions of contexts in which they appear, and relative entropy between those distributions is used as the similarity measure for clustering. Clusters are represented by average context distributions derived from the given words according to their probabilities of cluster membership. In many cases, the clusters can be thought of as encoding coarse sense distinctions. Deterministic annealing is used to find lowest distortion sets of clusters: as the an- nealing parameter increases, existing clusters become unstable and subdivide, yielding a hierarchi- cal "soft" clustering of the data. Clusters are used as the basis for class models of word coocurrence, and the models evaluated with respect to held-out test data.

Statistical methods for automatically extracting information about associations between words or documents from large collections of text have the potential to have considerable impact in a number of areas, such as information retrieval and natural-language-based user interfaces. However, even huge bodies of text yield highly unreliable estimates of the probability of relatively common events, and, in fact, perfectly reasonable events may not occur in the training data at all. This is known as the sparse data problem. Traditional approaches to the sparse data problem use crude approximations. We propose a different solution: if we are able to organize the data into classes of similar events, then, if information about an event is lacking, we can estimate its behavior from information about similar events. This thesis presents two such similarity-based approaches, where, in general, we measure similarity by the Kullback-Leibler divergence, an information-theoretic quantity. Our first approach is to build soft, hierarchical clusters: soft, because each event belongs to each cluster with some probability; hierarchical, because cluster centroids are iteratively split to model finer distinctions. Our clustering method, which uses the technique of deterministic annealing,

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