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Related Concept Videos

Physical Properties of Alkanes02:33

Physical Properties of Alkanes

Alkanes are nonpolar molecules due to the presence of only carbon and hydrogen atoms. The electronegativity difference between carbon and hydrogen is minimal, and hence alkanes have a zero dipole moment. This leads to the presence of only dispersion forces between the molecules. The strength of dispersion forces is dependent on the surface area of the molecules on which they act. Since the surface area increases with the molecular length for straight-chain alkanes, the dispersion forces also...
Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene.  The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes02:14

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

The low reactivity in alkanes can be attributed to the non-polar nature of C–C and C–H σ bonds. Alkanes, therefore, were  initially termed as “paraffins,” derived from the Latin words: parum, meaning “too little,” and affinis, meaning “affinity.”
Alkanes undergo combustion in the presence of excess oxygen and high-temperature conditions to give carbon dioxide and water. A combustion reaction is the energy source in natural gas, liquified petroleum gas (LPG), fuel oil, gasoline, diesel fuel, and...
Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is bonded to two hydrogen atoms...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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A New Straightforward Method for Lipophilicity (logP) Measurement using 19F NMR Spectroscopy
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Published on: January 30, 2019

ClogP(alk): a method for predicting alkane/water partition coefficient.

Peter W Kenny1, Carlos A Montanari, Igor M Prokopczyk

  • 1Grupo de Estudos em Química Medicinal, NEQUIMED, Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador Sancarlense 400, São Carlos, SP 13560-590, Brazil. pwk.pub.2008@gmail.com

Journal of Computer-Aided Molecular Design
|June 6, 2013
PubMed
Summary
This summary is machine-generated.

A new ClogP(alk) model predicts alkane/water partition coefficients using molecular surface area and functional group contributions. This method enhances predictions for molecular design, especially for drug-like molecules.

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Area of Science:

  • Computational chemistry
  • Quantitative structure-property relationships (QSPR)

Background:

  • Alkane/water partition coefficients (P(alk)) are crucial for molecular design but lack accessible data and prediction tools compared to 1-octanol/water equivalents.
  • Limited availability of prediction models hinders accurate assessment of P(alk) for various chemical entities.

Purpose of the Study:

  • Introduce a novel computational method for predicting alkane/water partition coefficients (P(alk)) directly from molecular structure.
  • Develop a predictive model, ClogP(alk), to address the limitations in existing P(alk) data and tools.

Main Methods:

  • The ClogP(alk) model is based on the strong correlation (R² = 0.987) between P(alk) and molecular surface area (MSA) for saturated hydrocarbons.
  • The model employs a perturbation approach, treating molecules as modified saturated hydrocarbons and quantifying functional group contributions to P(alk).
  • Functional group contributions and interactions (e.g., intramolecular hydrogen bonds) are defined using SMARTS notation for transparency and reproducibility.

Main Results:

  • The model demonstrated a strong relationship between P(alk) and MSA for saturated hydrocarbons.
  • Parameterization was performed using established P(alk) data, and validation was conducted on an external dataset of 100 alkane/water logP measurements, including many drug compounds.

Conclusions:

  • The developed ClogP(alk) model provides a reliable method for predicting alkane/water partition coefficients from molecular structure.
  • This tool is valuable for molecular design and drug discovery, offering improved accessibility to P(alk) predictions.