Authors: Harifi-Mood, Ali Reza; Masumpour, Marzieh Sadat; Gholami, Mohammad Reza

Source: Progress in Reaction Kinetics and Mechanism, Volume 31, Number 2, 2006 , pp. 117-127(11)

Publisher: Science Reviews 2000 Ltd

Abstract:

Aromatic nucleophilic substitution reaction kinetics of 2-chloro-3,5-dinitropyridine with aniline was studied in aqueous solutions of methanol, ethanol, and 2-propanol at room temperature. The obtained results for aqueous solutions indicate that the second-order rate constants are in order of 2-propanol>ethanol>methanol with a maximum at water mole fraction of 0.9. The influence of solvent parameters including normalized polarity (E_T^N), dipolarity/polarisability (π*), and hydrogen bond donor acidity (α) on the second-order rate constants were investigated and multiple regressions gave much better results with regard to single parameter regressions. Dipolarity/polarisability and hydrogen bond donor acidity of media demonstrate opposite effects on the reaction rate. The dipolarity/polarisability of media has a positive effect regarding to zwitterionic character of the reaction intermediate and the hydrogen bond donor acidity shows a negative effect because of hydrogen-bonding interactions between aniline and solvent molecules.

Keywords: solvent effects; solute-solvent interactions; aromatic nucleophilic substitution reactions

Document Type: Research article

DOI: http://dx.doi.org/10.3184/007967406779946937

Affiliations: 1: Department of Chemistry, Sharif University of Technology, P.O. Box 11365-9516, Tehran, Iran

Publication date: 2006-06-06

More about this publication?

• Progress in Reaction Kinetics & Mechanism is an international journal for the quarterly publication of both in-depth reviews and research articles.

  In-depth reviews are comprehensive accounts bringing together work from many sources with the aim of providing an article of lasting value that will become established as the reference source in the particular subject. Research articles, on the other hand, normally focus on a relatively new or recently developed field or technique giving a state-of-the-art account of the subject and may well refer to a narrower range of existing work. It covers the fields of kinetics and mechanisms of chemical processes in the gas phase and solution of both simple and complex systems.

• Editorial Board
• Subscribe to this Title
• ingentaconnect is not responsible for the content or availability of external websites

Related content

• In this: publication
• By this: publisher
• In this Subject: Analytical Chemistry ,  Physical & Theoretical Chemistry
• By this author: Harifi-Mood, Ali Reza ;  Masumpour, Marzieh Sadat ;  Gholami, Mohammad Reza

Website © Publishing Technology. Article copyright remains with the publisher, society or author(s) as specified within the article.

• Terms and conditions
• Privacy policy
• Information for advertisers