Automatic natural language processing that goes beyond the bag-of-words model requires an understanding of semantic and syntactic relationships between language components. This work attempts to address the following issues: 1) describe a set of Russian prepositional structures as an interconnected system; 2) collect corpus-based statistics reflecting preposition meanings and their hierarchy; and 3) describe meanings of prepositions acting as grammatical connectors for content words. Preposition meanings are described using categories based on G. A. Zolotova’s concept of syntaxeme. The results obtained are based on word frequencies extracted from corpora of contemporary Russian texts. This work describes the key objectives, approaches, methods, novelty, and findings of the research. The key findings include grammar and ontology of the main Russian prepositions, research into secondary prepositions (prepositions derived from content words), preposition database with a network interface, and a set of automated procedures aiding in ‘working out’ the meaning of a preposition.