Related Experiment Video
Updated: Jul 15, 2026
12:07
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Naphthalene-1,7-diol.
1Institute of Chemistry and Environment Protection, Jan Dlugosz University, al. Armii Krajowej 13/15, 42-200 Czestochowa, Poland. crystal@cz.onet.pl
Summary
This study reveals the crystal structure of C(10)H(8)O(2), detailing how molecules form chains through hydrogen bonds and pi-pi stacking. These interactions create a complex 3D network, offering insights into molecular assembly.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Understanding molecular interactions is key to designing new materials.
- Crystal engineering relies on predicting and controlling intermolecular forces.
- The compound C(10)H(8)O(2) presents an interesting case for studying hydrogen bonding and pi-stacking.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(10)H(8)O(2).
- To analyze the intermolecular interactions governing the crystal packing.
- To understand the formation of extended networks in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
- Analysis of hydrogen bonds (O-H...O, C-H...O) and pi-stacking interactions was performed.
- Non-covalent interaction analysis was employed to characterize the crystal packing.
Main Results:
- The asymmetric unit contains two independent, planar molecules of C(10)H(8)O(2).
- Molecules self-assemble into infinite chains of rings via O-H...O and C-H...O hydrogen bonds.
- Pi-pi stacking interactions reinforce these chains, and weak C-H...pi interactions connect adjacent chains.
Conclusions:
- The crystal structure is stabilized by a combination of hydrogen bonding and pi-stacking interactions.
- The observed network architecture highlights the importance of multiple non-covalent forces in crystal engineering.
- This detailed structural analysis provides a foundation for further studies on the properties and applications of C(10)H(8)O(2).
Related Concept Videos
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...
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.
01:18Aromatic Hydrocarbon Anions: Structural Overview
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
Due to the absence of continuous overlap of p...
01:57Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
01:16IUPAC Nomenclature of Aldehydes
Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
01:29UV–Vis Spectroscopy: Woodward–Fieser Rules
UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...