The Betti reaction is a straightforward three components condensation of 2-naphthol, an aryl aldehyde and an amine, that yield easily an aminobenzylnaphthol [1]. In previous work, we investigated the intermolecular interactions in the crystal structures of chiral aminobenzylnaphthols synthesized with this procedure [2]. The crystal packings of some cyclic phosphorus derivatives of these intermediates were also investigated [3]. The most peculiar interactions that we observed in all these molecules were many short distance CH···? interactions [2]. Moreover, we observed that the use of different p-halobenzaldehydes (X = F, Cl, Br) in the Betti reaction yielded almost isostructural aminobenzylnaphthols [2]. Now, we wish to report our investigation on the crystal packings of newly synthesized aminobenzylnaphthols deriving from a Betti reaction of 2-naphthol, aryl aldehydes and valine methyl ester (Scheme 1). Significant differences with our previous work were observed mainly due to the presence of a further hydrogen bonding acceptor in the molecules (the carbonyl oxygen atom of the valine moiety). Furthermore, we observed that different para-substitutions on the starting aryl aldehyde yielded crystal structures having different packings and new intermolecular interactions.

Intermolecular Interactions In The Crystal Packings Of Structurally Related Aminoacid Derivatives Synthesized Via A Betti Reaction

-
2015

Abstract

The Betti reaction is a straightforward three components condensation of 2-naphthol, an aryl aldehyde and an amine, that yield easily an aminobenzylnaphthol [1]. In previous work, we investigated the intermolecular interactions in the crystal structures of chiral aminobenzylnaphthols synthesized with this procedure [2]. The crystal packings of some cyclic phosphorus derivatives of these intermediates were also investigated [3]. The most peculiar interactions that we observed in all these molecules were many short distance CH···? interactions [2]. Moreover, we observed that the use of different p-halobenzaldehydes (X = F, Cl, Br) in the Betti reaction yielded almost isostructural aminobenzylnaphthols [2]. Now, we wish to report our investigation on the crystal packings of newly synthesized aminobenzylnaphthols deriving from a Betti reaction of 2-naphthol, aryl aldehydes and valine methyl ester (Scheme 1). Significant differences with our previous work were observed mainly due to the presence of a further hydrogen bonding acceptor in the molecules (the carbonyl oxygen atom of the valine moiety). Furthermore, we observed that different para-substitutions on the starting aryl aldehyde yielded crystal structures having different packings and new intermolecular interactions.
2015
X ray diffraction
weak interactions
aminoacids
Betti reactions
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14243/304084
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact