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Crystallographic evidence for intramolecular C−H...O interactions in principal nucleosides. Refinement of the crystal structure of thymidine

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Abstract

An analysis of crystallographic data for the major nucleosides has shown that their molecules (except for guanosine) exhibit specific intramolecular C−H...O interactions, which are weak hydrogen bonds. In purine nucleosides these interactions are rare and rather weak. For pyrimidine nucleosides, in addition to the previously known intramolecular interaction C6−H6...O5′, we have revealed the intramolecular interactions C1′−H1′...O2 and C6−H6...O1′. The three interactions make approximately equal contributions to the stabilization of the anti-conformation in pyrimidine nucleosides and make this conformation prevailing. To enhance the reliability of the results of studying the C−H...O interactions in thymidine, we performed an additional, more exact, X-ray diffraction analysis of the substance.

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Authors
  1. A. N. Chekhlov
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Additional information

Institute of Physiologically Active Substances, Russian Academy of Sciences, Chernogolovka. Translated fromZhurnal Strukturnoi Khimii, Vol. 36, No. 1, pp. 178–184, January–February, 1995.

Translated by I. Izvekova

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Chekhlov, A.N. Crystallographic evidence for intramolecular C−H...O interactions in principal nucleosides. Refinement of the crystal structure of thymidine. J Struct Chem 36, 155–161 (1995). https://doi.org/10.1007/BF02577763

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  • DOI: https://doi.org/10.1007/BF02577763

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