Untitled

doi:10.1039/b101078f

Cited by 1 publication

(1 citation statement)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…19 In the di-methyl 6-uracilmethylphosphonate (CSD refcode: XOJDUW), the synthon observed was very similar to S5 type but utilizing the N3−H3•••O4C4 bond. 62 The S1 or S2 type synthons were observed in 6-uracilmethylphosphonic acid (CSD refcode: BOXWOA), 75 6-(chloromethyl)pyrimidine-2,4(1H,3H)-dione (CSD refcode: SODLIJ), 76 6-chlorouracil (CSD refcode: SOZFEV), 77 6-iodouracil (CSD refcode: SOZFIZ), 77 6-uradinyl-4,4,5,5-tetramethyl-4,5-dihydro-1Himidazole-1-oxyl (CSD refcode: VAMXUD), 78 and 6-({bis-[(pyridin-2-yl)methyl]amino}methyl)pyrimidine-2,4(1H,3H)dione (CSD refcode: XOZWIV). 79 Molecular Dimers in the Crystal Structure of 3.…”

Section: ■ Introductionmentioning

confidence: 99%

Invariant and Variable Supramolecular Self-Assembly in 6-Substituted Uracil Derivatives: Insights from X-ray Structures and Quantum Chemical Study

Al-Wahaibi

Bysani

Tawfik

et al. 2021

Crystal Growth & Design

View full text Add to dashboard Cite

In this study, three new 6-(arylthio)uracil derivatives, namely, 6-(phenylthio)pyrimidine-2,4(1H,3H)-dione (1), C 10 H 8 N 2 O 2 S; 6-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione (2), C 11 H 10 N 2 O 2 S; and 6-(3,5-dimethylphenylthio)pyrimidine-2,4-(1H,3H)-dione (3), C 12 H 12 N 2 O 2 S, have been synthesized. Singlecrystal structures of these compounds reveal an invariant molecular tape contains alternate R 2 2 (8) synthons formed by N−H•••O hydrogen bonds in 1 and 3. This alternate hydrogen-bonded pattern disappeared in 2; instead, a new synthon is generated. The lattice energy calculation suggests that the methyl-substituted derivatives (2 and 3) have high stabilization energy than compound 1. The electrostatic potential map reveals the difference in the accepting tendency of the carbonyl oxygen. The Hirshfeld surface and 2D-fingerprint plots analyses demonstrate that the major intermolecular interactions come from H•••O contacts in 1, and these contacts were reduced due to the presence of methyl substitutions in 2 and 3. This reduction is compensated by the increase of the same amount of H•••H contacts in these structures. Further, the PIXEL energy and DFT calculations at the M06-2X-D3/cc-pVTZ level of theory were used to characterize the dimeric topology formed in structures of 1−3. The intermolecular interaction energies of dimers calculated by the PIXEL method were compared with the B97D3/def2-TZVP level of approximation. Although these molecules' crystal packing is somewhat different, the energy frameworks show similarities on the respective crystal structure's shortest axis. Furthermore, the nature and strength of various noncovalent interactions such as N−H•••O, C−H•••O/S/π, π•••π, and a chalcogen bond of type C−S•••OC were evaluated using the Bader's quantum theory of atoms-in-molecules framework.

show abstract