2-(4-Nitro-phen-yl)-5-phenyl-furan.
Zhi Guan1, Yan-Hong He, Gangqiang Wang
1School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China.
Summary
This study reveals the near-planar molecular structure of C(16)H(11)NO(3). Crystal analysis shows molecules forming ribbons via hydrogen bonds and pi-pi interactions, detailing its unique crystal packing.
Area of Science:
- Crystallography
- Molecular Structure Analysis
- Supramolecular Chemistry
Background:
- Understanding molecular arrangements in crystals is crucial for predicting material properties.
- Intermolecular forces, such as hydrogen bonds and pi-pi interactions, dictate crystal packing and stability.
Purpose of the Study:
- To determine the precise molecular and crystal structure of the title compound, C(16)H(11)NO(3).
- To investigate the intermolecular interactions governing the crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to analyze the molecular and crystal structure.
- Analysis of bond lengths, angles, and non-covalent interactions (hydrogen bonds, pi-pi stacking) was performed.
Main Results:
- The molecule C(16)H(11)NO(3) exhibits a nearly planar conformation with a small dihedral angle (2.73°) between its aromatic rings.
- Crystal packing is characterized by ribbon formation through intermolecular C-H⋯O hydrogen bonds along the [101] direction.
- Significant pi-pi interactions were observed between aromatic and furan rings of adjacent molecules, with short centroid-centroid distances (3.681(3) Å and 3.811(3) Å).
Conclusions:
- The study elucidates the detailed three-dimensional structure and intermolecular interactions of C(16)H(11)NO(3).
- The findings highlight the role of hydrogen bonding and pi-pi stacking in organizing molecules within the crystal lattice, contributing to supramolecular assembly.
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Related Concept Videos
01:13Five-Membered Heterocyclic Aromatic Compounds: Overview
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
02:23Structure and Nomenclature of Alcohols and Phenols
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
02:36Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
01:23Nomenclature of Aromatic Compounds with a Single Substituent
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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.
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.