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Hydrogen bonding patterns in salts of derivatives of aminopyrimidine and thiobarbituric acid.
- Source :
-
Acta Crystallographica Section B: Structural Science, Crystal Engineering & Materials . Apr2015, Vol. 71 Issue 2, p144-152. 9p. - Publication Year :
- 2015
-
Abstract
- Three salts, namely 2-amino-4,6-dimethylpyrimidin-1-ium thiobarbiturate trihydrate (I), 2-amino-4,6-dimethoxypyrimidin-1-ium thiobarbiturate dihydrate (II) and 2,4-diamino-5-(3′,4′,5′-trimethoxybenzyl)pyrimidin-1-ium thiobarbiturate (III), were synthesized and characterized by IR and X-ray diffraction techniques. The primary interaction between the acid and base happens via N-H...O hydrogen bonds in (II) and (III), and via water-mediated N-H...O W and O W-H W...S in (I). The water molecules present in compound (I) form a (H2O)12 water cluster via water-water interactions. In all three compounds (I)-(III), thiobarbiturate anions form self-complementary pairs with a robust R22(8) motif via a pair of N-H...O/N-H...S hydrogen bonds. They mimic the nucleobase base pairs by utilizing the same groups (thymine/uracil uses N3-H and C4=O8 groups during the formation of Watson-Crick and Hoogsteen base pairs with adenine). Compound (I) forms a water-mediated base pair through N-H...O W hydrogen bonds and forms an R42(12) motif. The formation of N-H...S hydrogen bonds, water-mediated base pairs and water-water interactions in these crystal systems offers scope for these systems to be considered as a model in the study of hydration of nucleobases and water-mediated nucleobase base pairs in macromolecules. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 20525192
- Volume :
- 71
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Acta Crystallographica Section B: Structural Science, Crystal Engineering & Materials
- Publication Type :
- Academic Journal
- Accession number :
- 101894541
- Full Text :
- https://doi.org/10.1107/S2052520615001729