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Crystal Structure of a Hydrated Molecular 1 : 2 Complex of Nicotinamide Adenine Dinucleotide (NAD + ) and Gallic Acid: Polar Alignment of the Phenolic Partner Molecules
Author(s) -
Ermer Otto,
Neudörfl Jörg
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200017
Subject(s) - chemistry , nad+ kinase , nicotinamide adenine dinucleotide , crystal structure , molecule , adduct , crystallography , stereochemistry , pincer movement , pyridine , organic chemistry , enzyme , catalysis
Nicotinamide adenine dinucleotide (oxidized form, free acid, NAD + ) was utilized as an auxiliary for polar alignment of gallic acid (=3,4,5‐trihydroxybenzoic acid, GA) in the crystalline molecular complex NAD + ⋅(GA) 2 ⋅(H 2 O) 5 . In this adduct, NAD + takes up a novel U‐shaped conformation accepting a GA molecule to give rise to a pincer‐type π ‐complex. With the assistance of further GA molecules, these pincer assemblies build up infinite donoracceptor π ‐stacks in the crystal. An extended network of H‐bonds among the multitude of pertinent active functional groups and the water molecules supports the crystal structure. These findings may imply noteworthy material properties, in particular nonlinear optical effects, and might also serve to trigger inspiring biochemical connections to be made. The crystal structure of anhydrous GA is also reported, which is centrosymmetric and non‐polar.