Related Experiment Video
Updated: May 26, 2026

11:01
Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
(1-Adamant-yl)(3-amino-phen-yl)methanone
Acta Crystallographica. Section E, Structure Reports Online
|December 27, 2011
Summary
The crystal structure of C(17)H(21)NO reveals molecular packing stabilized by hydrogen bonds and weak interactions. The study details the compound's structure and bonding characteristics.
Area of Science:
- Crystallography
- Molecular structure analysis
- Chemical bonding
Background:
- Understanding molecular packing is crucial for predicting material properties.
- Intermolecular forces significantly influence crystal lattice formation and stability.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(17)H(21)NO.
- To analyze the intermolecular interactions and their role in molecular packing.
- To investigate the electronic conjugation within the molecule.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of hydrogen bonds (N-H⋯O) and weak interactions (N-H⋯π) was performed.
- Torsion angles were measured to assess the degree of conjugation.
Main Results:
- The crystal structure of C(17)H(21)NO was determined, showing molecular packing along the b axis.
- Intermolecular N-H⋯O hydrogen bonds and N-H⋯π interactions were identified as key stabilizing forces.
- A torsion angle of 27.1° was observed between the carbonyl group and the benzene ring, indicating attenuated conjugation.
Conclusions:
- The molecular packing in C(17)H(21)NO is primarily governed by hydrogen bonding and π-interactions.
- The observed twisting reduces electronic conjugation between the carbonyl group and the benzene ring.
- The findings provide insights into the structure-property relationships of this compound.
More Related Videos
Related Concept Videos
Mass Spectrometry of Amines
In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule; a molecule with an odd number of nitrogen atoms produces a molecular ion with an odd molecular weight. Amines undergo fragmentation through α cleavage, producing nitrogen-containing cations—iminium ions—and alkyl radicals. Mass spectra of aromatic and cyclic aliphatic amines exhibit strong molecular ion peaks, but acyclic aliphatic amines show...
Preparation of 1° Amines: Gabriel Synthesis
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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.
Amines: Introduction
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...

