2-(4-Methoxy-phen-yl)-4,5-dihydro-1H-imidazole
Summary
This study reveals the molecular structure of C(10)H(12)N(2)O, highlighting a nearly planar arrangement. The molecule forms one-dimensional chains through hydrogen bonding in its crystal structure.
Area of Science:
- Crystallography
- Molecular Chemistry
Background:
- Understanding molecular geometry is crucial for predicting chemical properties.
- Crystal structure analysis provides insights into intermolecular interactions.
Purpose of the Study:
- To determine the precise three-dimensional structure of the molecule C(10)H(12)N(2)O.
- To investigate the intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to analyze the crystal structure.
- Geometric parameters, including dihedral angles and interatomic distances, were precisely measured.
Main Results:
- The dihedral angle between the benzene and imidazole rings is 14.86(16)°.
- An intramolecular distance of 2.54 Å was observed between an ortho-H atom and a nitrogen atom.
- Intermolecular N-H⋯N hydrogen bonds link molecules into 1D chains along the a axis.
Conclusions:
- The molecule exhibits an approximately planar conformation.
- The crystal packing is dominated by hydrogen bonding, leading to the formation of extended chains.
Related Concept Videos
Basicity of Heterocyclic Aromatic Amines
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

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