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Inductive Effects on Chemical Shift: Overview01:27

Inductive Effects on Chemical Shift: Overview

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The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...
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Isomerism in Alkenes

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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

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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.
14.3K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.7K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
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17.5K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Is there a trend in inductive effect for different alkyl groups?

Mark C Elliott1, Colan E Hughes1, Peter J Knowles1

  • 1School of Chemistry, Cardiff University Park Place Cardiff CF10 3AT UK elliottmc@cardiff.ac.uk.

RSC Advances
|June 26, 2025
PubMed
Summary
This summary is machine-generated.

This study found no significant difference in the inductive effects of common alkyl groups using Hirshfeld charge analysis. Alkyl group electronegativity did not correlate with electron-donating or withdrawing abilities, suggesting Hirshfeld charges are more reliable for charge distribution analysis.

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Area of Science:

  • Computational chemistry
  • Organic chemistry

Background:

  • Understanding the electronic effects of alkyl groups is crucial in organic chemistry.
  • Traditional methods like electronegativity may not accurately reflect charge distribution.

Purpose of the Study:

  • To compare the inductive effects of four representative alkyl groups.
  • To evaluate the correlation between alkyl group properties and their electronic influence.
  • To determine the reliability of Hirshfeld charge analysis versus other methods for assessing charge distribution.

Main Methods:

  • Hirshfeld charge analysis was employed to quantify charge distribution.
  • Calculated charges were compared across different alkyl groups.
  • Alkyl group electronegativity values were assessed for correlation.

Main Results:

  • No significant differences were observed in the inductive effects of the studied alkyl groups via Hirshfeld analysis.
  • Alkyl group electronegativity showed a poor correlation with electron-donating/withdrawing abilities.
  • A significant divergence was noted between 13C NMR chemical shifts and calculated Hirshfeld charges.

Conclusions:

  • Hirshfeld charge analysis provides a more reliable measure of charge distribution than alkyl group electronegativity.
  • 13C NMR chemical shifts may not directly reflect the electronic effects indicated by Hirshfeld charges.