Intramolecular interactions governing the conformational behavior of 2-aminopropan-1-ol and its methyl ether: hydrogen bonding, gauche effect, and metallic interactions

Understanding the conformations of amino alcohols is crucial for their applications in fields such as medicinal chemistry and environmental science. Therefore, the conformational analysis of 2-aminopropan-1-ol ( 1 ) and its methyl ether 2 was performed both quantum-chemically and experimentally, using infrared and NMR spectroscopies. The conformational equilibrium of 1 is primarily governed by an N∙∙∙H–O intramolecular hydrogen bond. In contrast, its methyl ether derivative lacks this hydrogen-bonding capability and has negligible O∙∙∙H–N interactions, thus the gauche effect driven by antiperiplanar hyperconjugative interactions dictates its conformational balance. Our study reveals that both types of intramolecular interactions are overridden upon coordination to Zn 2+ and Cd 2+ ions. These findings suggest that intramolecular interactions in 1 and 2 are insufficient to prevent chelation with these cations in various systems. This research provides insights into the behavior of these compounds in complex systems and their potential applications in heavy metal remediation.