Solid-State Supramolecular Structures of Resorcinol−Arylboronic Acid Compounds

Abstract

[structure: see text] An X-ray crystallographic study of unique hydrogen-bonded supramolecular solid-state networks comprised of a tetraarylboronic acid resorcinarene is described. When 1 is recrystallized from 9:1 MeOH:EtOH, partial esterification takes place to give compound 2, the corresponding half methyl ester, which forms an infinite two-dimensional array. Each molecule participates in 12 hydrogen bonds with other macrocycles. These hydrogen bonds are both B-OH- - - OH (phenolic) and OH (phenolic)- - -OH (phenolic).

Structural, Antioxidant and Antivarial Studies of C-3-nitrophenyl CALIX[4]resorcinarene

“…The dihedral angle between the resorcinol ring (C1-C6) and 3nitrophenyl linkage group (C8-C13) is 87.4(3)°, indicate a high degree of co-planarity between the resorcinol rings and lead to the adoption of a chair conformation. A similar conformation with approximately C 2h symmetry due to the presence of a crystallographic inversion center has also been observed for tetraarylboronic acid resorcinarene [10].…”

“…The biological application of calixarene derivatives has currently become an interest to many researchers world-wide [6]. One major problem for the application in certain field is its low solubility and flexible existence of their conformers [7][8][9][10]. The presence of more than one conformer in the solution can be determined by NMR studies.…”

Synthesis and Crystal Structure of a Ternary Lattice Inclusion System of C‐4‐acetamidophenylcalix[4]‐2‐methylresorcinarene dimethylsulfoxide tetrasolvate dihydrate

“…However, the resorcinol ring (C1C6) forms a dihedral angle of 83.83(13)° and 74.74(13)° with the (C9C14) and (C25C30) rings, respectively. The bond lengths and angles (Table ) are in normal ranges and comparable to those in tetraarylboronicacidcalix[4]resorcinarene …”

2-(Methoxycarbonyl)phenylboronic acid

“…The use of arylboronic acids in supramolecular assembly is potentially promising (Fournier et al, 2003;Davis et al, 2001) but still relatively unexplored. Arylboronic acids with carbonyl substituents are interesting as they may be able to support supramolecular organization via hydrogen-bonding interactions.…”