TY - JOUR
AU - Clark, C., Randall
AB - Abstract The aqueous solution conformation of a series of isomeric hydroxymethoxybenzamides is evaluated b y reversed-phase liquid chromatography. The structure-retention relationship studies demonstrate the existence of intramolecular hydrogen bond formation when the substituent groups are positioned ortho to the amide side chain. The formation of N-H…O and N-H…O associations produces enhanced reversed-phase retention relative to those substitution patterns that preclude intramolecular associations. The N-H…O association formed in N-ethyl-2-methoxy-4-hydroxybenzamide produces a higher capacity factor than the 3,5-isomers. The 2-hydroxy-4-methoxy isomer has a much higher capacity factor than the 2-methoxy-4-hydroxybenzamide, perhaps because of the position of the unassociated-associated equilibrium or the relative strength of the N-H…O association. The 2-hydroxy-6- methoxybenzamide displays the highest capacity factor, which is likely the result of simultaneous formation of both N-H…O and N-H…O associations. The relative retention of these isomeric benzamides is consistent on several hydrocarbon stationary phases and at elevated temperatures. This content is only available as a PDF.
TI - Liquid Chromatographic Studies on Intramolecular Hydrogen Bonding in Hydroxy-Methoxybenzamides Model Compounds Related to Remoxipride Metabolites
JO - Journal of Chromatographic Science
DO - 10.1093/chromsci/29.4.153
DA - 1991-04-01
UR - https://www.deepdyve.com/lp/oxford-university-press/liquid-chromatographic-studies-on-intramolecular-hydrogen-bonding-in-EOR4jDcrYx
SP - 153
EP - 157
VL - 29
IS - 4
DP - DeepDyve
ER -