Solid State Structure and Intermolecular Interactions of two N-Benzylidenephenylethylamines

This article describes single crystal X-ray diffraction studies of two Schiff bases containing hydroxyl groups in aromatic rings: N -(4-hydroxybenzylidene)phenylethylamine ( 1 ) and N -(4-hydroxy-3-methoxybenzylidene)tyramine ( 2 ). Molecules of compound 1 , with just one phenolic OH group, adopted...

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Bibliographic Details
Published in:Journal of chemical crystallography 2020-09, Vol.50 (3), p.206-211
Main Authors: Chaves, Sebastián, Pérez-Redondo, Adrián, Quevedo, Rodolfo
Format: Article
Language:English
Subjects:
Aromatic compounds
Chains
Chemical bonds
Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Hydrogen bonding
Hydrogen bonds
Hydroxyl groups
Imines
Inorganic Chemistry
Organometallic Chemistry
Original Paper
Phenylethylamine
Physical Chemistry
Single crystals
Solid state
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Summary:This article describes single crystal X-ray diffraction studies of two Schiff bases containing hydroxyl groups in aromatic rings: N -(4-hydroxybenzylidene)phenylethylamine ( 1 ) and N -(4-hydroxy-3-methoxybenzylidene)tyramine ( 2 ). Molecules of compound 1 , with just one phenolic OH group, adopted an anti conformation, and were associated in zigzag chains with O–H···N hydrogen bonds between the azomethine fragment and the hydroxyl group. However, a gauche conformation was preferred by compound 2 , which contained two hydroxyl groups in aromatic rings. Molecules of 2 were arranged in a three-dimensional array through O–H···N and O–H···O hydrogen bonding interactions. The results highlighted the importance of OH positions in the aromatic ring for the structural behaviour of the Schiff bases derived from phenylethylamines. Graphical Abstract Molecules of Schiff bases containing the moiety ArCH=N–CH 2 CH 2 Ar with one or two hydroxyl groups in the para position in the aromatic rings are associated in zigzag chains in the solid state through O–H···N hydrogen bonding interactions.
ISSN:1074-1542
1572-8854
DOI:10.1007/s10870-019-00792-7