Water molecules in hydroxy/acid networks as a competition between dynamics and bonding. Synthesis of a wet hydrophobic pore.
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.
Pérez-Hernández
Natalia
N
Instituto de Investigaciones Químicas, CSIC, Americo Vespucio, s/n, Isla de La Cartuja, 41092, Sevilla, Spain.
Pérez
Cirilo
C
Rodríguez
Matías L
ML
Foces-Foces
Concepción
C
Tolstoy
Peter M
PM
Limbach
Hans H
HH
Morales
Ezequiel Q
EQ
Pérez
Ricardo
R
Martín
Julio D
JD
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*
D002264:Carboxylic Acids; D006880:Hydroxy Acids; D008051:Lipid Bilayers; D014867:Water