6533b7defe1ef96bd12769a2
RESEARCH PRODUCT
The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT, and AIM study
Satu IkonenBorys OśmiałowskiMagdalena KowalskaArto ValkonenErkki Kolehmainensubject
chemistry.chemical_classification010405 organic chemistryStereochemistryHydrogen bondIntermolecular forceSubstituentCrystal structure010402 general chemistryCondensed Matter Physics01 natural sciences0104 chemical scienceschemistry.chemical_compoundCrystallographychemistryMoietyPhysical and Theoretical ChemistryPolarization (electrochemistry)Single crystalAlkyldescription
The single crystal structures of two 2-acylaminopyrimidines, where alkyl groups in acyl moiety are iso-propyl (1) and dichloromethyl (2), were solved by X-ray diffraction method. The strength of intermolecular hydrogen bonding interactions depends on the C–H bond polarization increased by exchanging two methyl groups by chlorine atoms in the adjacent substituent. The computational methods provide an additional insight into the intermolecular interactions and are utilized in explaining the differences in the observed crystal structures. The experimental and computational data together explain the differences in the formed aggregates and revealed that these simple substitutions cause crucial changes in the intermolecular interactions. Introduction of nitrogen atom instead of CH moiety completely changes the aggregation.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-05-16 | Structural Chemistry |