Chromogenic Charge Transfer Cleft-Type Tetrahydrobenzoxanthene Enantioselective Receptors for Dinitrobenzoylamino Acids

• Published in: Journal of organic chemistry Vol. 69; no. 20; pp. 6883 - 6885
• Main Authors: Oliva, Ana I, Simón, Luis, Muñiz, Francisco M, Sanz, Francisca, Ruiz-Valero, Caridad, Morán, Joaquín R
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-10-2004
• Subjects: Chemistry; Chromogenic Compounds; Dinitrobenzenes - chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Models, Molecular; Organic chemistry; Preparations and properties; Receptors, Amino Acid - chemistry; Stereoisomerism; Xanthenes - chemistry; Nitro compound; Enantioselectivity; Molecular structure; Molecular interaction; Receiver; Experimental study; Oxygen heterocycle; X ray diffraction; Thin layer chromatography; Racemic; Aminoacid; Aromatic compound; Inclusion compound; Charge transfer; Chromophore
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo049113h

A combination of a benzoxanthene cleft-type receptor with an electron-rich aromatic ring capable of establishing charge-tranfer interactions provides enantioselective receptors for dinitrobenzoylamino acids. Racemic mixtures of the receptor can be resolved with TLCs impregnated with the guest. The structure of the complexes has been established in an X-ray study. Enantiomeric amino acids provide complexes with different colors.