title: Water molecules in hydroxy/acid networks as a competition between dynamics and bonding. Synthesis of a wet hydrophobic pore.
abstract: In a model formed by hydroxy acids with a general structure (+/-)-1, we found that solid-state structures depend on steric interactions. Thus, with the exception of molecules 1b and 1e, compounds (+/-)-1a-(+/-)-1m, which possess bulky and conformationally rigid substituents, aggregate by forming tapes and sheets by alternating (+) and (-) subunits held together via carboxylic acid to alcohol hydrogen bonds. Homologue (+/-)-1n with conformationally flexible substituents, which allow conformational deformation gives, by way of the incorporation of water molecules, an efficient hexagonal assembly, which extends to the third-dimension to form tubular H-bonding networks. Each puckered channel can be described as being interconnected by closely packed hexagons in chair-like conformations. The ethyl groups presented in (+/-)-1n provided the volume required to lock the inner hexagonal wall into a rigid structure.
authors.affiliation: Instituto de Investigaciones Químicas, CSIC, Americo Vespucio, s/n, Isla de La Cartuja, 41092, Sevilla, Spain.
authors.forename: Natalia
authors.initials: N
authors.lastname: Pérez-Hernández
authors.forename: Cirilo
authors.initials: C
authors.lastname: Pérez
authors.forename: Matías L
authors.initials: ML
authors.lastname: Rodríguez
authors.forename: Concepción
authors.initials: C
authors.lastname: Foces-Foces
authors.forename: Peter M
authors.initials: PM
authors.lastname: Tolstoy
authors.forename: Hans H
authors.initials: HH
authors.lastname: Limbach
authors.forename: Ezequiel Q
authors.initials: EQ
authors.lastname: Morales
authors.forename: Ricardo
authors.initials: R
authors.lastname: Pérez
authors.forename: Julio D
authors.initials: JD
authors.lastname: Martín
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry / Q000378:metabolism; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D006880:Hydroxy Acids / Q000737:chemistry*; D008051:Lipid Bilayers; D008958:Models, Molecular; D008968:Molecular Conformation; D014867:Water / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D006880:Hydroxy Acids; D008051:Lipid Bilayers; D014867:Water