title: Crystalline arrays of side chain modified bile acids derivatives. Two novel self-assemblies based on π-π and belly-to-belly interactions.
abstract: Crystalline derivatives of side chain modified bile acids were efficiently prepared from the naturally occurring steroids by palladium-catalyzed cross coupling reaction as a key step. The solvent-free crystalline bile acids derivatives 2b-e are readily accessed by slow evaporation from selected solvents. A variety of steroidal scaffolds were found and elucidated by SXRD studies. The crystal packing of the title compounds are dominated by hydrogen-bonding interactions established between differently positioned acetyl protecting groups, which in the case of 2b and 2e take advantage of the facial amphiphilicity producing two novel steroidal supramolecular self-assemblies combining π-π and strong facial interactions. Thus, these crystalline arrays of side chain modified bile acids represent promising scaffolds for research and implementation in biomolecular materials or inclusion phenomena.
authors.affiliation: Facultad de Química, Departamento de Química Orgánica, Universidad Nacional Autónoma de México, 04510 Ciudad de México, Mexico.
authors.forename: Martha C
authors.initials: MC
authors.lastname: Mayorquín-Torres
authors.affiliation: Instituto de Ciencias Nucleares, Departamento de Química de Radiaciones y Radioquímica, Universidad Nacional Autónoma de México, 04510 Ciudad de México, Mexico.
authors.forename: Rafael
authors.initials: R
authors.lastname: Arcos-Ramos
authors.affiliation: Facultad de Química, Departamento de Química Orgánica, Universidad Nacional Autónoma de México, 04510 Ciudad de México, Mexico.
authors.forename: Marcos
authors.initials: M
authors.lastname: Flores-Álamo
authors.affiliation: Facultad de Química, Departamento de Química Orgánica, Universidad Nacional Autónoma de México, 04510 Ciudad de México, Mexico. Electronic address: martin.iglesias@unam.mx.
authors.forename: Martín A
authors.initials: MA
authors.lastname: Iglesias-Arteaga
mesh_terms: D001647:Bile Acids and Salts / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D014961:X-Ray Diffraction
chemical_list: D001647:Bile Acids and Salts
keywords: Crystalline arrays; Side chain modified bile acids; Single X-ray diffraction; Steroidal supramolecular self-assemblies; π-Stacking