Related Experiment Video
Updated: May 22, 2026
08:48
Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
Published on: January 26, 2016
[2-(1H-Indol-4-yl)eth-yl]dipropyl-amine.
De-Cai Wang1, Hua-Yang Pan, Jun-Song Song
1State Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China.
Summary
This study details the molecular structure of a novel organic compound, C(16)H(24)N(2), revealing an orthogonal orientation of its amine group relative to the indole core. Molecular analysis also identified specific hydrogen bonding in its crystalline form.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Indole derivatives are prevalent in pharmaceuticals and natural products, making their structural characterization important.
- The conformation of aliphatic substituents can significantly influence molecular packing and intermolecular interactions.
Purpose of the Study:
- To elucidate the precise molecular geometry of the title compound, C(16)H(24)N(2).
- To investigate the spatial relationship between the aliphatic amine substituent and the indole ring system.
- To characterize the intermolecular interactions and crystal packing in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
- Analysis of torsion angles and bond lengths provided insights into the molecule's conformation.
- Identification of hydrogen bonding patterns using crystallographic data.
Main Results:
- The aliphatic amine substituent exhibits an orthogonal orientation relative to the indole plane, with a C-C-C-C torsion angle of 75.7(3)°.
- The amine nitrogen atom displays a pyramidal configuration, deviating by 0.380(3) Å from planarity.
- All aliphatic groups adopt extended transoid conformations, and molecules form chains via N-H⋯N hydrogen bonds in the crystal lattice.
Conclusions:
- The study provides a detailed structural description of C(16)H(24)N(2), highlighting significant conformational features.
- The observed orthogonal orientation and pyramidal amine geometry are key structural characteristics.
- The identified hydrogen bonding network dictates the crystal packing, influencing the solid-state behavior of the compound.
Related Concept Videos
01:17Nomenclature of Primary Amines
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
01:28Preparation 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...
01:10Nomenclature 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.
01:29Preparation of Amides
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
01:07Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.