ISSN:
1573-904X
Keywords:
lidocaine
;
conformations
;
infrared (IR)
;
nuclear magnetic resonance (NMR)
;
hydrogen bonding
;
partition coefficients
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract IR and 1H NMR studies in CDCl3 and CCl4 of a series of tertiary aminoxylidides with the amino group in the 2 to 6 position of the acyl chain are described. Lidocaine, diethylaminoaceto-2′,6′-xylidide, forms an intramolecular five-membered ring hydrogen-bonded monomer at all concentrations in both solvents. β-Diethyl-amino-propiono-2′,6′-xylidide forms an intramolecular six-membered ring hydrogen-bonded monomer in CDCl3 and CCl4 but a trans intermolecularly associated species is the major form present at high concentrations in CCl4. The longer-chain homologues are mixtures of nonassociated trans and cis monomers at low concentrations but associated trans forms predominate at high concentrations. Evidence for the presence of a hydrogen-bonded seven-membered ring intramolecular monomer in CDCl3 for γ-diethylaminobutyro-2′,6′-xylidide is presented. The relationship between the molecular conformation and the partition coefficient is discussed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1015805023987
Permalink