title: Synthesis and characterization of two sulfonated resorcinarenes: a new example of a linear array of sodium centers and macrocycles.
abstract: Two sulfonated resorcinarenes were synthesized by reacting C-tetra(butyl) resorcinarene or C-tetra(2-(methylthio)ethyl)resorcinarene with formaldehyde in the presence of sodium sulfite. Their structures were determined via FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. Thermal gravimetric analyses of the derivatives were also carried out and revealed the presence of water molecules in the solid state. The sulfonated product of C-tetra(butyl)resorcinarene was characterized by an X-ray crystal structure determination. The asymmetric unit contains eight molecules of water and two of acetone, and analysis indicated that sulfonated resorcinarene prefers a cone configuration (rccc conformation) in the solid state. In the crystal array, classical hydrogen bond interactions O-H···O and intermolecular contacts were observed. In the crystal packing, a linear array of capsules of sulfonated resorcinarenes was generated for a chain of sodium atoms and sulfonate groups.
authors.affiliation: Departamento de Química, Universidad de los Andes, Cr. 1 No. 18A 10, Bogotá 111711, Colombia. e.sanabria84@uniandes.edu.co.
authors.forename: Edilma
authors.initials: E
authors.lastname: Sanabria
authors.affiliation: Química Física, Universidad de Alcalá, Alcalá de Henares 28871, Spain. miguel.esteso@uah.es.
authors.forename: Miguel Ángel
authors.initials: MÁ
authors.lastname: Esteso
authors.affiliation: Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Alcalá de Henares 28871, Spain. adrian.perez@uah.es.
authors.forename: Adrián
authors.initials: A
authors.lastname: Pérez-Redondo
authors.affiliation: Departamento de Química, Universidad de los Andes, Cr. 1 No. 18A 10, Bogotá 111711, Colombia. edvargas@uniandes.edu.co.
authors.forename: Edgar
authors.initials: E
authors.lastname: Vargas
authors.affiliation: Departamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Cr. 30 No. 45-03, Bogotá 111321, Colombia. mmaldonadov@unal.edu.co.
authors.forename: Mauricio
authors.initials: M
authors.lastname: Maldonado
mesh_terms: D000096:Acetone / Q000737:chemistry; D000476:Alkanesulfonates / Q000138:chemical synthesis*; D047250:Calixarenes / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D005557:Formaldehyde / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012995:Solubility; D013447:Sulfites / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D000476:Alkanesulfonates; D013447:Sulfites; C466160:resorcinarene; D014867:Water; D047250:Calixarenes; D000096:Acetone; D005557:Formaldehyde; D010649:Phenylalanine; C025026:sodium sulfite
keywords: cone conformation; sulfonation; water soluble resorcinarene