title: X-ray structure of a trimeric 5,5'-biaryl/erythro-beta-O-4-ether lignin model: evidence for through-space weak interactions.
abstract: The crystal structure of a trimeric lignin model 1 presenting the characteristic pattern of biphenyl (5,5') and aryl-alkyl-ether (beta-O-4) linkages has been determined. The crystal system is triclinic and the crystallographic unit cell consists of two monomeric molecules. These results are compared with crystal data from the literature of simple models of the 5,5' and beta-O-4 structure type. The availability of a terminal aldehyde function on the model affords some interesting intermolecular interactions by weak hydrogen bonding which controls the conformation of the molecule and the aromatic ring orientation in particular; an unexpected cisoïd conformation of the biaryl unit is observed based on the 64.4 degrees value found for the torsion angle between the two 5,5' aromatic rings.
authors.affiliation: Laboratoire de Synthèse et Physicochimie de Molécules d'Intérêt Biologique, CNRS, Université Paul-Sabatier, Toulouse, France.
authors.forename: J P
authors.initials: JP
authors.lastname: Roblin
authors.forename: H
authors.initials: H
authors.lastname: Duran
authors.forename: E
authors.initials: E
authors.lastname: Duran
authors.forename: L
authors.initials: L
authors.lastname: Gorrichon
authors.forename: B
authors.initials: B
authors.lastname: Donnadieu
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry*; D003461:Crystallography; D018360:Crystallography, X-Ray; D019281:Dimerization; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D006860:Hydrogen Bonding; D008031:Lignin / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D011108:Polymers; D013816:Thermodynamics
chemical_list: C408388:1-(3-methoxy-4-tert-butyldimethylsilyloxy-5-(2-tert-butyldimethylsilyloxy-3-methoxy-5-hydroxymethylphenyl)phenyl)-2-(4-formyl-2-methoxyphenoxy)-1,3-propanediol; D000438:Alcohols; D000447:Aldehydes; D001713:Biphenyl Compounds; D006841:Hydrocarbons, Aromatic; D017646:Organosilicon Compounds; D011108:Polymers; D008031:Lignin