Supramolecular motifs in 1-(2-cyanoethyl)thymine and 1-(3-cyanopropyl)thymine.
In both 1-(2-cyanoethyl)thymine [systematic name: 3-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)propanenitrile], C(8)H(9)N(3)O(2), (I), and 1-(3-cyanopropyl)thymine [systematic name: 4-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)butanenitrile], C(9)H(11)N(3)O(2), (II), the core of the supramolecular structure is formed by centrosymmetric dimers generated by N-H...O hydrogen bonds. Further weak hydrogen bonds of C-H...O and C-H...N types generate molecular tapes and sheets that resemble those in uracil and its methyl derivatives. The steric hindrance that arises from the cyanoalkyl substituents perturbs the conformations of the tapes and sheets.
Borowiak
Teresa
T
Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland. borowiak@amu.edu.pl
Dutkiewicz
Grzegorz
G
Spychała
Jarosław
J