Research Article

Correlation of the rates of solvolysis of 2-furancarbonyl chloride and three naphthoyl chlorides

  1. Malcolm J. D'Souza1,*,
  2. Mary E. Boggs1,
  3. Dennis N. Kevill2

Article first published online: 5 JAN 2006

DOI: 10.1002/poc.1010

Issue

Journal of Physical Organic Chemistry

Journal of Physical Organic Chemistry

Volume 19, Issue 3, pages 173–178, March 2006

Additional Information

How to Cite

D'Souza, M. J., Boggs, M. E. and Kevill, D. N. (2006), Correlation of the rates of solvolysis of 2-furancarbonyl chloride and three naphthoyl chlorides. J. Phys. Org. Chem., 19: 173–178. doi: 10.1002/poc.1010

Author Information

  1. 1

    Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA

  2. 2

    Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, USA

*Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA.

Publication History

  1. Issue published online: 30 MAR 2006
  2. Article first published online: 5 JAN 2006
  3. Manuscript Accepted: 5 OCT 2005
  4. Manuscript Revised: 4 OCT 2005
  5. Manuscript Received: 19 AUG 2005

Funded by

  • NIH NCRR INBRE. Grant Number: 2P20 RR016472

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Keywords:

  • extended Grunwald–Winstein equation;
  • solvolysis;
  • 2-furancarbonyl chloride;
  • naphthoyl chlorides

Abstract

The correlations of the specific rates of solvolysis of the title compounds using extended forms of the Grunwald–Winstein equation are consistent with the overall picture which is emerging for acyl chloride solvolyses, with competing addition–elimination (with rate-determining addition) and ionization (assisted by nucleophilic solvation) pathways. Except in the more ionizing solvents of low nucleophilicity, 2-furancarbonyl chloride follows the addition–elimination pathway, in contrast to 2-thiophenecarbonyl chloride. Except in solvents of highest nucleophilicity and low ionizing power, the solvolyses of the naphthoyl chlorides (1-naphthoyl, 2-naphthoyl and 6-methyl-2-naphthoyl) all favor the ionization pathway. In the correlation of the 1-naphthoyl chloride solvolyses, there is a slight improvement when a term governed by the sensitivity to changes in the aromatic ring parameter (hI) is incorporated; this can be associated with a rather minor steric hindrance involving the peri-hydrogen. Copyright © 2006 John Wiley & Sons, Ltd.

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