Foundations of chemical microscopy. 3. Derivatives of some chiral phenylalkylamines and phenylalkylamino acids with 5-nitrobarbituric acid.

At one time, 5-nitrobarbituric acid (also known as dilituric acid) was extensively used as a chemical reagent for the qualitative identification of a variety of basic substances by light microscopy. This methodology was based on evaluation of observed crystal morphologies, because skilled observers could associate a unique crystal habit with the products formed with analytes when those were crystallized using standardized methods. As part of a study to understand the scientific foundations that permitted chemical microscopy to function as a useful analytical technique during its heyday, the products formed by dilituric acid with resolved and racemic phenylalkylamines and phenylalkylamino acids were characterized using a variety of physical analytical techniques. It was found that the different crystal morphologies associated with each of the crystalline adducts were derived from the ability of the systems to form differing structural types and/or hydrate crystal forms upon crystallization.