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Related Concept Videos

Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Related Experiment Video

Updated: May 22, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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4,7,8-Trimethyl-2H-chromen-2-one.

Jian-Xin Yang, Xue-Mei Tan, Xiang-Hui Wang

    Acta Crystallographica. Section E, Structure Reports Online
    |May 17, 2012
    PubMed
    Summary

    This study reveals the crystal structure of a C(12)H(12)O(2) molecule, highlighting its planar nature and intermolecular interactions. Key findings include anti-parallel pi-pi stacking and C-H...O hydrogen bonds influencing crystal packing.

    Area of Science:

    • Crystallography
    • Solid-state chemistry
    • Molecular structure analysis

    Background:

    • Understanding molecular arrangement in crystals is crucial for predicting material properties.
    • Intermolecular forces, such as pi-pi stacking and hydrogen bonding, dictate crystal lattice formation.
    • The specific compound C(12)H(12)O(2) has not been previously characterized in terms of its detailed solid-state structure.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C(12)H(12)O(2).
    • To investigate the intermolecular interactions governing the packing of these molecules in the solid state.
    • To provide a detailed description of the molecular planarity and crystal architecture.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional atomic arrangement.

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  • Analysis of atomic coordinates and bond lengths/angles to assess molecular geometry.
  • Intermolecular contact analysis, including pi-pi stacking and hydrogen bonding, was performed.

    • Main Results:

    • The molecule C(12)H(12)O(2) exhibits a nearly planar conformation, with minimal deviation of non-hydrogen atoms from the mean plane.
    • The crystal structure is dominated by anti-parallel pi-pi stacking interactions along the c-axis, with short centroid-centroid distances of 3.866 Å.
    • C-H...O hydrogen bonds link molecules into extended ribbons along the a-axis, further stabilizing the crystal lattice.

    Conclusions:

    • The C(12)H(12)O(2) molecule adopts a planar structure in the solid state.
    • The crystal packing is significantly influenced by a combination of pi-pi stacking and C-H...O hydrogen bonding.
    • These findings contribute to the understanding of structure-property relationships in organic crystalline materials.