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The article suggests that V. Vinogradov’s definition of ‘predicativity’ as the constitutive feature of a sentence is not a purely technical linguistic concept, but rather, a philosophical one, grounded in Kant’s transcendental categories of pure reason. Exposing the philosophical background of Vinogradov’s approach to syntax enables an exploration of the different aspects of the meaning of a sentence that is shaped by its ‘predicativity’. In particular, the interpretation of this concept given in the article leads to a more flexible model of the relation between the structural and functional (communicative) aspects of a sentence. The coexistence of these two contradictory yet mutually dependent aspects of a sentence’s meaning is compared with S. I. Karcevsky’s idea of the ‘asymmetrical dualism’ of the verbal sign. © 2014, Springer Science+Business Media Dordrecht.