Predicting the outcome of imine formation


Objectives

  1. The main objective is to predict the amount of imine precipitated based on solubility measurements and predictions.
  2. Aromatic amines are known to give more stable imines so these will be studied first.
  3. Aromatic aldehydes do not participate in aldol self-condensation so these will be studied first.
  4. A secondary objective is to predict the rate of imine formation in a given solvent at a known concentration.

Tasks to do

  1. Find the solubility of doubly aromatic imines from the literature. This is the basic substructure search. (using Beilstein substructure search)
  2. Find the melting points of doubly aromatic imines from the literature. This is the basic substructure search. (using Beilstein substructure search)
  3. List the aromatic aldehydes and aromatic amines in the lab.

Tasks done

  1. Substructure searches on Beilstein were performed. The exact parameters of the query can be seen here. 14 hits were found from the query, however all were discarded because either they had disubstituted imines, metals or only had solubility information in water.
  2. Substructure search on Scifinder were performed. Under explore reactions, the reaction of aniline and benzaldehyde to form benzalaniline was drawn. 94 hits were found. The third hit was a report from an experiment: Synthesis and investigation of π-conjugated azomethine self-assembled multilayers by layer-by-layer growth. This experiment contained a method for the synthesis of benzalaniline from aniline and benzaldehyde and was the basis for this synthesis in Usefulchem Exp261.