Related Experiment Video
Updated: Jun 1, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
4-{[3-(4-Hydroxy-benzyl-ideneamino)-2,2-dimethyl-propyl]iminiomethyl}phenolate dihydrate
Abstract:
The asymmetric unit of the title compound, C(19)H(22)N(2)O(2)·2H(2)O, comprises a zwitterionic form of the Schiff base compound and two water mol-ecules of crystallization. Inter-molecular N-H⋯O, C-H⋯O and O-H⋯N hydrogen bonds involving one of the water mol-ecules in the asymmetric unit generate seven- and eight-membered rings, with R(2) (1)(7) and R(2) (2)(8) ring motifs, respectively. The dihedral angle beween the two aromatic rings is 86.5 (2)°. The imino and iminium groups are coplanar with the benzene rings to which they are attached, making dihedral angles (N-C-C-C) of -179.3 (5) and -179.2 (4)°, respectively. Validation software indicates the higher symmetry space group Pnma for this structure. However, this process ignores H atoms and the zwitterionic configuration of the main mol-ecule breaks the higher symmetry. Solution in Pna2(1) provides a chemically sensible zwitterionic compound with improved residuals. In the crystal structure, mol-ecules are linked together through inter-molecular O-H⋯O, O-H⋯N, N-H⋯O and C-H⋯O inter-actions, forming a three-dimensional network. The crystal structure is further stabilized by inter-molecular C-H⋯π inter-actions.
Related Concept Videos
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Structure and Nomenclature of Alcohols and Phenols
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Hydrolysis of Chlorobenzene to Phenol: Dow Process
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Benzene to Phenol via Cumene: Hock Process

