The article deals with the semantic and syntactic properties of Russian disjunctive conjunctions li... li..., ili, libo, to... to..., ne to... ne to..., to li... to li... based on the peculiarities of their structure. The etymology of each conjunction is established on the basis of particles in their structure. The relationship between their initial meanings and the role they play in the structure of conjunctions is investigated. This approach is based on the principles of nonparadigmatic linguistics, the object of which are particles-primary nontaxonomic lexemes, which function in the linguistic system from the time of its formation. The original semantics of such particles is preserved in the structure of modern lexemes formed with their participation. This is the so-called hidden memory of the language. It helps the speaker and hearer to distinguish between the variants of the lexemes and synonyms; the differences between them are not easily described by means of the traditional interpretation. As a result of the study, the following results are obtained. The element li determines the presence of different shades of uncertainty and questioning in the semantics and pragmatics of the conjunctions li... li..., ili. The element ne in ne to... ne to... is also connected with the semantics of uncertainty, but this semantics is built on the basis of contrast and opposition of the coordinating propositions. The sub-element i in the conjuntion ili adds the semantics of connection, enumeration and development of narration to the relations between propositions. The element to in to... to... and to li... to li... performs a deictic function related both to the idea of a shift in the narrative and to the general pointing to something, which is correlated with the semantics of temporarity (to... to...) or uncertainty (ne to... ne to..., to li... to li...). The conjunction libo derived from the ancient conjunction lyubo, which, in turn, derived from the short form of the corresponding adjective. The adjective lyubo bears the semantics of desire, which passed on to the conjunction lyubo. Subsequently, the conjunction lyubo phonetically changed under the influence of the conjunctions with the element li (li... li..., ili). The semantics of desire remained with it at a deep syntax level. In this regard, the conjunction libo has the meaning of the preferred choice of one of the proposed alternatives. Generally, the meanings and syntactic features of Russian disjunctive conjunctions are still inextricably linked with the semantics and categorical properties of their initial structural elements, on which their modern distinctive features are based. Due to this, Russian disjunctive conjunctions express very subtle and differentiated shades of disjunctive relations.