Experimental and theoretical studies of molecular complexes of theophylline with some phenylboronic acids. Issue 49 (3rd May 2016)

• Record Type: Journal Article
• Authors: TalwelkarShimpi, Mayura; Öberg, Sven; Giri, Lopamudra; Pedireddi, V. R.
• Is Part Of: RSC advances. Volume 6:Issue 49(2016)
• Page Start: 43060
• Page End: 43068
• Publication Date: 2016-05-03
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra04100k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Molecular complexes of active pharmaceutical ingredient theophylline with p -substituted-chloro, -bromo, -iodo and -hydroxyphenylboronic acids as well as 1, 4-phenylene-bis-boronic acid have been reported. Abstract : Molecular complexes of the active pharmaceutical ingredient (API) theophylline, 1 with 4-halophenylboronic acids [4-chlorophenylboronic acid (a ), 4-bromophenylboronic acid (b ), 4-iodophenylboronic acid (c )], 4-hydroxyphenylboronic acid (d ) and 1, 4-phenylene-bis-boronic acid (e ) have been reported. The complexes were characterized and analysed using the intensity data obtained by X-ray diffraction techniques. All the halo substituted boronic acid complexes are found to be isostructural (1.a, 1.b and1.c ) irrespective of the variations in size and electronegativity of halogen atoms while complexes with non-halogenated boronic acids, 1.d and1.e, show distinctly different features between themselves as well as with that of1.a–c, both in two and three-dimensional arrangements. Complexes1.a–c are noted to be crystallized in the form of sheet structures, which are stacked in three dimensional arrangements, while channels and square grid networks are observed in1.d and1.e, respectively. Further the homomeric and heteromeric interactions which occur in the complexes have been analysed by a DFT-D3 method.