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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
N,N-Bis(2-pyridylmeth-yl)-tert-butyl-amine
Allen Mambanda1, Deogratius Jaganyi, Kirsty Stewart
1School of Chemical and Physical Sciences, University of KwaZulu-Natal, Scottsville 3209, South Africa.
Summary
This study details the crystal structure of a pyridine compound, C(16)H(21)N(3). Molecules form layers via C-H⋯π interactions, with a near 90° angle between pyridine rings.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the solid-state behavior of organic molecules is crucial for materials science.
- Pyridine derivatives are important in pharmaceuticals and materials.
- Intermolecular interactions dictate crystal packing and material properties.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound C(16)H(21)N(3).
- To analyze the spatial arrangement of pyridine rings within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of the crystal structure revealed the dihedral angle between pyridine rings and intermolecular interactions.
Main Results:
- The dihedral angle between the two pyridine rings in C(16)H(21)N(3) was determined to be 88.11(9)°.
- Intermolecular C-H⋯π interactions were identified as the primary driving force for crystal packing.
- These interactions lead to the formation of a layered structure parallel to the (10) plane.
Conclusions:
- The crystal structure of C(16)H(21)N(3) is characterized by a near-orthogonal arrangement of its pyridine rings.
- C-H⋯π interactions play a significant role in organizing the molecules into extended layers.
- This structural insight contributes to the understanding of crystal engineering with pyridine-based compounds.
Related Concept Videos
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.
01:28Preparation 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...
01:25Basicity 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).
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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...
01:17Nomenclature 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.