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Kinetics and mechanism of the addition of iodine monochloride to some alkenes in nitrobenzene solvent. Effect of polarity of the solvent

Kinetik und Mechanismus der Addition vonICl zu einigen Alkenen in Nitrobenzol als Lösungsmittel. Effekt der Polarität des Lösungsmittels

Monatshefte für Chemie / Chemical Monthly volume 115, pages 35–43 (1984)Cite this article

Abstract

The kinetics of the addition of iodine monochloride (ICl) to some vinyl compounds in nitrobenzene solvent was investigated. In all cases the reaction follows second order dependence on ICl and first order on the substrate, making the total order three. Rate constants were measured for each substrate at 20°, 30°, 40° and 50°C.Arrhenius plots were made from which activation energies were evaluated. Other kinetic and thermodynamic parameters are reported. A suitable mechanism is proposed for the reaction and based on this, the various parameters are discussed. Solvent effects are discussed and the data with nitrobenzene and acetic acid solvents are compared.

Zusammenfassung

Die Kinetik der Addition von ICl zu einigen Vinylverbindungen in Nitrobenzol als Lösungsmittel wurde untersucht. In allen Fällen ist die Reaktion von zweiter Ordnung hinsichtlich ICl und von erster Ordnung hinsichtlich des Substrats, d. h. mit einer Gesamtordnung von drei. Geschwindigkeitskonstanten wurden für jedes Substrat bei 20°, 30°, 40° und 50°C gemessen. AusArrhenius-Diagrammen wurden Aktivierungsenergien ermittelt und auch andere kinetische und thermodynamische Parameter wurden bestimmt. Ein Mechanismus wird vorgeschlagen, wobei die verschiedenen Parameter diskutiert werden. Lösungsmitteleffekte werden ebenfalls diskutiert und die Daten mit Nitrobenzol und Essigsäure als Lösungsmittel miteinander verglichen.

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Authors and Affiliations

  1. Department of Physical Chemistry, University of Madras, 600 025, Madras, India

    Nagarajan Amirtha, Seshaiyer Viswanathan & Ramachandran Ganesan

Authors
  1. Nagarajan Amirtha
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  2. Seshaiyer Viswanathan
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  3. Ramachandran Ganesan
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Amirtha, N., Viswanathan, S. & Ganesan, R. Kinetics and mechanism of the addition of iodine monochloride to some alkenes in nitrobenzene solvent. Effect of polarity of the solvent. Monatsh Chem 115, 35–43 (1984). https://doi.org/10.1007/BF00798419

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  • DOI: https://doi.org/10.1007/BF00798419

Keywords

  • Iodine monochloride
  • Kinetics
  • Solvent effects