N,N'-Di-8-quinolyladipamide
Shi-Ying Wang1, Xing-Lei Xie, Qing-Hua Huang
1College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China.
Summary
This study details the crystal structure of a C24H22N4O2 molecule, revealing its planar quinoline and hexyl groups. Molecular symmetry and hydrogen bonding influence its unique crystal packing and stability.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Crystal structure analysis provides precise details about molecular geometry, conformation, and intermolecular interactions.
Purpose of the Study:
- To elucidate the complete molecular structure of the title compound, C24H22N4O2.
- To analyze the planarity of the quinoline ring system and hexyl chain and their relative orientation.
- To identify and characterize intra-molecular hydrogen bonding and analyze crystal packing forces.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Crystallographic symmetry operations, including inversion centers, were analyzed.
- Geometric parameters such as dihedral angles and hydrogen bond distances were measured.
Main Results:
- The molecule C24H22N4O2 possesses a crystallographic inversion center at the midpoint of the central C-C bond.
- The quinoline ring system and hexyl chain are nearly planar, with a dihedral angle of 46.30(2)° between them.
- Intra-molecular hydrogen bonds (N-H⋯N and C-H⋯O) form five- and six-membered rings, and crystal packing is stabilized by C-H⋯O interactions.
Conclusions:
- The crystal structure of C24H22N4O2 is defined by its molecular symmetry and specific intra-molecular interactions.
- The observed planarity and dihedral angle are key features of this molecule's conformation.
- Intermolecular C-H⋯O interactions play a significant role in stabilizing the overall crystal lattice.
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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.
01:16IUPAC Nomenclature of Carboxylic Acids
IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
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