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Updated: Jun 1, 2026
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
N-(2-Pyridylmethanimidamido)pyridine-2-carboximidamide
1Ordered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China.
Summary
This study analyzes the molecular structure of C(12)H(12)N(6), revealing specific dihedral angles and hydrogen bonding. Intramolecular bonds create planar stability, while intermolecular bonds form chains.
Area of Science:
- Crystal engineering
- Supramolecular chemistry
- Organic chemistry
Background:
- Understanding molecular conformation is crucial for designing materials with specific properties.
- Hydrogen bonding plays a key role in directing molecular assembly and crystal packing.
- The dimethan-imine-hydrazine core offers potential for diverse intermolecular interactions.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title molecule C(12)H(12)N(6).
- To investigate the role of intramolecular and intermolecular hydrogen bonds in stabilizing the molecular conformation and directing crystal packing.
- To analyze the dihedral angles between pyridine rings and the central core.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of dihedral angles provided insights into the molecule's conformation.
- Identification and analysis of intra- and intermolecular hydrogen bonds (N-H⋯N) were performed.
Main Results:
- The molecule C(12)H(12)N(6) exhibits distinct dihedral angles of 0.30(3)° and 13.94(3)° between pyridine rings and the central dimethan-imine-hydrazine group.
- Two intramolecular N-H⋯N hydrogen bonds stabilize a planar conformation of one pyridine ring.
- The other pyridine ring and an N-bonded H atom are rotated, forming intermolecular N-H⋯N chains propagating in the [010] direction.
Conclusions:
- The crystal structure is dictated by a combination of intramolecular stabilization and intermolecular chain formation via hydrogen bonding.
- The observed hydrogen bonding patterns influence the overall supramolecular architecture.
- This detailed structural analysis provides a foundation for understanding structure-property relationships in related compounds.
Related Concept Videos
01:25Basicity 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).
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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...
01:17Nomenclature 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.
01:10Nomenclature 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.
01:23Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...