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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.
Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Published on: January 19, 2016

Methyl 4-(cyclopropylmethoxy)-3-hydroxybenzoate [corrected].

Jing-Jing Hou1, Xian-Chao Cheng, Run-Ling Wang

  • 1School of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary
This summary is machine-generated.

The crystal structure of C(12)H(14)O(4) reveals a 60.3° dihedral angle between its benzene and cyclopropyl rings. Molecules form chains via intermolecular hydrogen bonds in the solid state.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Intermolecular interactions, such as hydrogen bonding, play a significant role in dictating crystal packing and material characteristics.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(12)H(14)O(4).
  • To determine the spatial relationship between the benzene and cyclopropyl rings within the molecule.
  • To identify and characterize the intermolecular interactions present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to collect diffraction data.
  • The crystal structure was solved and refined using standard crystallographic software.
  • Analysis of the structure included determination of bond lengths, bond angles, and dihedral angles, as well as identification of hydrogen bonding networks.

Main Results:

  • The crystal structure of C(12)H(14)O(4) was successfully determined.
  • A significant dihedral angle of 60.3(4)° was observed between the planar benzene ring and the cyclopropyl ring.
  • Molecules are organized into one-dimensional chains through intermolecular O-H⋯O hydrogen bonds, oriented along the [101] crystallographic direction.

Conclusions:

  • The study provides precise geometric information about the title compound's molecular conformation.
  • The identified hydrogen bonding network highlights the role of intermolecular forces in directing crystal assembly.
  • This structural data serves as a foundation for further investigations into the compound's physical and chemical behavior.