Selective inclusion crystallization of phenol derivatives with tetraalkylammonium salts

The Effects of Molecular Conformation and Chain Length in Complexes of Tetra-n-alkylammonium Halide with Nonplanar Aromatic Molecule

“…The bond lengths and angles of BNP in TBAB/BNP are in the range from 1.358 (2) to 1.430 (18) Å for C-C, from 117.7 (13) The C-C bond joining the two naphthol rings in TBAB/BNP and TPAB/BNP are 1.494 (18), 1.497 (2) Å, respectively, which are not significantly longer than the corresponding racemate conformation (1.475) [20,22]. The bond lengths and angles in tetrabutylammonium and tetrapentylammonium cations are within the accepted limits and not significantly different from those reported on tetrabutylammonium bromide [23] and crystal complexes of tetrabutylammonium bromide with phenol [11], tetrabutylammonium bromide with catechol [12]. The bond lengths and angles in tetrabutylammonium cation are in the range from 1.514 (2) to 1.531 (2) Å for C-C, from 108.2 (13) to 113.9 (13) o for C-C-C, from 1.518 (18) …”

“…They are also of interest due to different combinations of conformational and orientational disorder possible, depending on the lengths of the alkyl chains. The molecular aggregation between alkylammonium salts and organic molecules is of importance in the mechanistic study of the role of membranes [4], and separation of phenol derivatives [5]. Since, the interactions between alkylammonium halides and organic molecules play important roles in biological systems, separation science and technology, the complexes of alkylammonium halides with organic molecules are being studied by many supramolecular chemists.…”

“…. ) with nonplanar aromatic molecules, no studies have ever been done as per revealed by Cambridge Structural Database version 5.34, 2013. A further search of the Cambridge Structural Database for tetrabutylammonium halides (R 4 N + .X − , where R = butyl and X = Br or Cl) with phenol derivatives and other planar or nonplanar aromatic molecules revealed that only two complexes viz; tetrabutylammonium bromide complex with phenol [11] and catechol [12] have been reported.…”

Die Bildung von Riesenliposomen aus kristallinen Komplexen von Monoalkylammoniumtensiden und 4-Hydroxybiphenyl

“…Dieser Zugang hat den offensichtlichen Vorteil, daû der Vorläufer des C-Rings identisch mit dem des A-Rings ist (2). Die Durchführbarkeit der Methode wurde anhand der Synthese des Modellchromophors [3] demonstriert: Mit der Sulfidkontraktions/Iminoestercyclisierungs-Methode von Eschenmoser und Mitarbeitern [4] wurde ein Octahydroporphyrin-Vorläufer aufgebaut, der dann in einer doppelten Retroaldol/Oxidationssequenz zum Chromophor der Tolyporphine weiterreagierte. Hier berichten wir über eine Erweiterung dieser Route zur erfolgreichen Totalsynthese der vorgeschlagenen Struktur 1 b von ()-Tolyporphin-A-O,O-diacetat, woraus sich die Notwendigkeit einer neuen Festlegung der Struktur für diese Naturstoffklasse ergibt.…”

Crystal Structure of a Benzyltrimethylammonium Chloride Complex with <i>rac</i>-1,1′-Bi-2-naphthol: The Generation of Weak Interactions by the Influence of a Benzyl Group

“…The supramolecular and crystal engineering approach have become popular due to its pharmaceutical significance, as well as its application in separation science, and biomembrane studies. Typically, many supramolecular chemists and crystal engineers have extensively reported on molecular recognition studies between phenol derivatives and quaternary alkyl ammonium salts using an inclusion crystallization technique, 2,3 as well as a crystal engineering approach that involves the manipulation of hydrogen bonding patterns and packing fashions. 4 Such studies have been utilized in employing knowledge concerning the separation of phenol derivatives in both chemical and pharmaceutical industries.…”