Related Experiment Video
Updated: Jun 1, 2026
09:04
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Amino-guanidinium hydrogen succinate
Summary
This study details the molecular salt of amino-guanidinium and succinate, revealing its nearly planar cation structure and specific dihedral angle. Crystal packing analysis identified key intermolecular hydrogen bonds.
Area of Science:
- Crystallography
- Materials Science
- Chemical Physics
Background:
- Molecular salts are crucial in various chemical applications.
- Understanding the structural properties of ionic compounds is essential for predicting their behavior.
- Amino-guanidinium and succinate are components with potential for novel material development.
Purpose of the Study:
- To characterize the crystal structure of the amino-guanidinium succinate molecular salt.
- To determine the planarity of the amino-guanidinium cation and the dihedral angle with the succinate anion.
- To investigate the intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to analyze the molecular structure.
- Crystallographic data were used to calculate bond lengths, angles, and deviations from planarity.
- Analysis of hydrogen bonding networks was performed based on the determined atomic positions.
Main Results:
- The title compound, amino-guanidinium succinate (CH(7)N(4)(+)·C(4)H(5)O(4)(-)), was structurally characterized.
- The amino-guanidinium cation was found to be nearly planar, with a maximum deviation of 0.035(1) Å.
- A small dihedral angle of 3.35(6)° was observed between the cation and the succinate anion, indicating close association.
- Intermolecular N-H⋯O and O-H⋯O hydrogen bonds were identified as key features of the crystal packing.
Conclusions:
- The study provides a detailed structural description of amino-guanidinium succinate.
- The observed planarity of the cation and the specific dihedral angle offer insights into the molecular conformation.
- The identified hydrogen bonding network highlights the stabilizing interactions within the crystal structure, relevant for materials design.
Related Concept Videos
01:19Structure 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...
01:12Nomenclature of Secondary and Tertiary Amines
The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
01:23Amines to Sulfonamides: The Hinsberg Test
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
01:19Depolarizing Blockers: Pharmocokinetics
Depolarizing blockers are administered through intravenous injection. Succinylcholine is the most common choice of depolarizing blockers in emergency clinical practices. Although they have a rapid onset, they readily diffuse away from the motor end plate into the extracellular fluid. They are metabolized by enzymes such as liver butyrylcholinesterase and plasma pseudocholinesterases. This produces a short duration of action, typically 5-10 minutes long, unlike nondepolarizing blockers, which...
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.
03:46Qualitative Analysis
For solutions containing mixtures of different cations, the identity of each cation can be determined by qualitative analysis. This technique involves a series of selective precipitations with different chemical reagents, each reaction producing a characteristic precipitate for a specific group of cations. Metal ions within a group are further separated by varying the pH, heating the mixture to redissolve a precipitate, or adding other reagents to form complex ions.
For instance, group IV...
For instance, group IV...