Hydrogen bonding versus π-interactions: their key competition in sildenafil solvates. Issue 32 (5th July 2018)

• Record Type: Journal Article
• Authors: Barbas, Rafael; Prohens, Rafel; Font-Bardia, Mercè; Bauzá, Antonio; Frontera, Antonio
• Is Part Of: CrystEngComm. Volume 20:Issue 32(2018)
• Page Start: 4526
• Page End: 4530
• Publication Date: 2018-07-05
• Subjects: Crystals -- Periodicals; Crystal growth -- Periodicals; Crystallography -- Periodicals; Cristaux -- Périodiques; Cristaux -- Croissance -- Périodiques; Cristallographie -- Périodiques; 548
• DOI: 10.1039/c8ce00567b
• Languages: English
• ISSNs: 1466-8033

Abstract

Abstract : Herein we report the X-ray characterization of four sildenafil solvates where the conformation of the pyrazolo[3, 4- d ]pyrimidine and phenyl rings depends on the solvent. Abstract : Herein we report the X-ray characterization of four sildenafil solvates where the conformation of the pyrazolo[3, 4- d ]pyrimidine and phenyl rings depends on the solvent. It conditions the formation of an apparently innocent intramolecular H-bond that has a remarkable influence on the solid state architecture of the sildenafil solvates. DFT calculations indicate that a delicate balance between the energies of H-bonding and π–π (or lp–π) interactions are crucial.