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A Competitive Molecular Recognition Study: Syntheses and Analysis of Supramolecular Assemblies of 3,5‐Dihydroxybenzoic Acid and Its Bromo Derivative with Some N‐Donor Compounds
Author(s) -
Varughese Sunil,
Pedireddi Venkateswara Rao
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500570
Subject(s) - adduct , chemistry , supramolecular chemistry , hydrogen bond , moiety , stacking , stereochemistry , molecular recognition , molecule , derivative (finance) , crystal structure , crystallography , organic chemistry , financial economics , economics
A molecular recognition study of 3,5‐dihydroxybenzoic acid ( 1 ) and its bromo derivative 4‐bromo‐3,5‐dihydroxybenzoic acid ( 2 ) with the N‐donor compounds 1,2‐bis(4‐pyridyl)ethene (bpyee), 1,2‐bis(4‐pyridyl)ethane (bpyea), and 4,4′‐bipyridine (bpy) is reported. Thus, the syntheses and structural analysis of molecular adducts 1 a – 1 c ( 1 with bpyee, bpyea, and bpy, respectively) and 2 a – 2 c ( 2 with bpyee, bpyea, and bpy, respectively) are discussed. In all these adducts, recognition between the constituents is established through either OH⋅⋅⋅N and/or OH⋅⋅⋅N/CH⋅⋅⋅O pairwise hydrogen bonds. In all the adducts both OH and COOH functional groups available on 1 and 2 interact with the N‐donor compounds, except in 2 a , in which only COOH (COO − ) is involved in the recognition process. The COOH moieties in 1 a , 1 b , and 2 b form only single OH⋅⋅⋅N hydrogen bonds, whereas in 1 c and 2 c , they form pairwise OH⋅⋅⋅N/CH⋅⋅⋅O hydrogen bonds. In addition, subtle differences in the recognition patterns resulted in the formation of cyclic networks of different dimensions. In fact, only 1 c forms a four‐molecule cyclic moiety, as was already documented in the literature for this kind of assemblies. All complexes have been characterized by single‐crystal X‐ray diffraction. The supramolecular architectures are quite elegant and simple, with stacking of sheets in all adducts, but a rather complex network with a threefold interpenetration pattern was found in 2 c .