Related Experiment Video
Updated: May 27, 2026
09:45
Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
1-(2-Amino-eth-yl)-3-phenyl-thio-urea
Pramod Pansuriya1, Holger B Friedrich, Glenn E M Maguire
1School of Chemistry, University of KwaZulu-Natal, Durban, 4000, South Africa.
Acta Crystallographica. Section E, Structure Reports Online
|November 8, 2011
Summary
The crystal structure of C(9)H(13)N(3)S reveals molecules linked by hydrogen bonds, forming tape-like structures. This arrangement influences the spatial orientation between the phenyl ring and the thiourea group.
Area of Science:
- Crystallography
- Materials Science
- Chemical Physics
Background:
- Understanding molecular interactions is crucial for designing novel materials.
- Hydrogen bonding plays a significant role in supramolecular chemistry and crystal engineering.
- Thiourea derivatives are versatile building blocks in various chemical applications.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(9)H(13)N(3)S.
- To investigate the intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
- To determine the conformational preferences of the molecule in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
- Analysis of hydrogen bonding networks (N-H⋯S and N-H⋯N) was performed.
- Geometric parameters, including dihedral angles, were precisely measured.
Main Results:
- The crystal structure of C(9)H(13)N(3)S was successfully determined.
- Molecules are organized into hydrogen-bonded tapes along the b-axis through N-H⋯S and N-H⋯N interactions.
- A dihedral angle of 44.9(2)° was observed between the phenyl ring and the thiourea moiety.
Conclusions:
- The study provides detailed insights into the solid-state structure and hydrogen bonding patterns of C(9)H(13)N(3)S.
- The observed tape structures highlight the importance of hydrogen bonding in directing molecular assembly.
- The conformational data contributes to understanding the structure-property relationships of thiourea derivatives.
Related Concept Videos
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...
01:07Preparation 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.
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.
01:29Preparation 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...
01:22Preparation of 1° Amines: Azide Synthesis
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
02:26Preparation and Reactions of Sulfides
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.