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Published on: June 23, 2019
N-(Pyridin-2-ylmeth-yl)pyridin-2-amine
Summary
This study details the crystal structure of a nitrogen-containing organic compound, C(11)H(11)N(3). Molecular geometries are similar, with minor differences in torsion angles and dihedral angles between pyridyl rings, stabilized by intermolecular hydrogen bonds and pi-interactions.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the solid-state behavior of organic molecules is crucial for materials science.
- C(11)H(11)N(3) is a compound with potential applications in various chemical fields.
- Crystal structure analysis provides insights into molecular packing and intermolecular interactions.
Purpose of the Study:
- To determine and analyze the crystal structure of the title compound, C(11)H(11)N(3).
- To investigate the molecular geometry and intermolecular interactions within the crystal lattice.
- To understand the factors contributing to crystal packing stability.
Main Methods:
- Single-crystal X-ray diffraction was employed to elucidate the crystal structure.
- Analysis of crystallographic data included determination of molecular geometry, torsion angles, and dihedral angles.
- Identification and analysis of intermolecular interactions such as hydrogen bonds and C-H···π interactions.
Main Results:
- The title compound, C(11)H(11)N(3), crystallizes with two molecules (A and B) in the asymmetric unit.
- Molecular geometries of A and B are highly similar, with notable differences in C-N-C-C torsion angles (67.4(5)° and -69.3(5)°).
- Dihedral angles between pyridyl ring planes are 84.0(2)° (A) and 83.2(2)° (B); crystal packing is stabilized by N-H⋯N hydrogen bonds and C-H⋯π interactions.
Conclusions:
- The crystal structure of C(11)H(11)N(3) reveals subtle conformational differences between molecules in the asymmetric unit.
- Intermolecular hydrogen bonding and C-H⋯π interactions play a significant role in stabilizing the crystal lattice.
- The findings provide fundamental structural information relevant to the solid-state properties and potential applications of this compound.
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.
01:25Basicity 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).
01:17Nomenclature 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.
01:26Physical Properties of Amines
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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...