An Adjustable Cleft Based on an 8‐Sulfonamide‐2‐Naphthoic Acid with Oxyanion Hole Geometry

Cleft type receptors showing the oxyanion hole motif have been prepared in a straightforward synthesis starting from the commercial 3,7‐dihidroxy‐2‐naphthoic acid. The double H‐bond donor pattern is achieved by the introduction of a sulfonamide group in the C‐8 position of naphthalene and a carboxam...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2021-10, Vol.27 (59), p.14605-14609
Main Authors: Garrido‐González, José J., Boya del Teso, Irene, Fuentes de Arriba, Ángel L., Sanz, Francisca, Martín del Valle, Eva M., Morán, Joaquín R., Alcázar, Victoria
Format: Article
Language:English
Subjects:
Acetic acid
Antibiotics
Aromatic compounds
carboxylic acids
Charge transfer
Chemistry
Crystal structure
Hydrogen bonding
Hydrogen bonds
molecular recognition
Naphthalene
NMR
Nuclear magnetic resonance
oxyanion hole
Receptors
Sulfonamides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Cleft type receptors showing the oxyanion hole motif have been prepared in a straightforward synthesis starting from the commercial 3,7‐dihidroxy‐2‐naphthoic acid. The double H‐bond donor pattern is achieved by the introduction of a sulfonamide group in the C‐8 position of naphthalene and a carboxamide at the C‐2 position. This cleft, for which the geometry resembles that of an oxyanion hole, is able to adjust to different guests, as shown by the analysis of the X‐ray crystal structures of associates with methanol or acetic acid. Combination of hydrogen bonds and charge‐transfer interactions led to further stabilization of the complexes, in which the electron‐rich aromatic ring of the receptor was close in space to the electron‐deficient dinitroaromatic guests. Modelling studies and bidimensional NMR experiments have been carried out to provide additional information. The torsion angle around the sulfonamide bond gives these oxyanion hole‐like receptors a variable size cleft. As stronger H‐bonds imply shorter distances between H‐bond donors and acceptors, these clefts with sulfonamide and carboxamide functions might be of interest in catalysis. X‐ray crystal structures confirm the formation of two strong linear H‐bonds between the NHs and carbonyl or alcohol oxygens, showing the adaptability of the cleft.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202102137