A Caltech Library Service

Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist

Su, Julius T. and Goddard, William A., III (2005) Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist. Journal of the American Chemical Society, 127 (41). pp. 14146-14147. ISSN 0002-7863. doi:10.1021/ja054446x.

[img] PDF (Coordinates, energies, and frequency data for compounds referenced (PDF), and crystal structure and NMR shift comparisons) - Supplemental Material
See Usage Policy.


Use this Persistent URL to link to this item:


A rearrangement of hypervalent bonds, or twisting, proves to be the rate-determining step in the 2-iodoxybenzoic acid (IBX) oxidation of alcohols. From this insight, derived from density functional theory calculations, we explain why IBX oxidizes large alcohols faster than small ones and propose a modification to the reagent predicted to make it more active.

Item Type:Article
Related URLs:
URLURL TypeDescription Information
Goddard, William A., III0000-0003-0097-5716
Additional Information:© 2005 American Chemical Society. Received July 5, 2005. Publication Date (Web): September 15, 2005. We thank the NSF (predoctoral fellowship to J.T.S. and CTS-0132002) and the DOE (DE-PS36-03GO93015) for financial support. We thank Prof. Brian M. Stoltz and Dr. Jonas Oxgaard for useful discussions concerning the mechanism of the reaction and constrained alcohol−IBX complexes.
Funding AgencyGrant Number
NSF Predoctoral FellowshipUNSPECIFIED
Department of Energy (DOE)DE-PS36-03GO93015
Issue or Number:41
Record Number:CaltechAUTHORS:20170420-132741288
Persistent URL:
Official Citation:Enhancing 2-Iodoxybenzoic Acid Reactivity by Exploiting a Hypervalent Twist Julius T. Su and William A. Goddard III Journal of the American Chemical Society 2005 127 (41), 14146-14147 DOI: 10.1021/ja054446x
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76780
Deposited By: Tony Diaz
Deposited On:20 Apr 2017 20:36
Last Modified:15 Nov 2021 17:02

Repository Staff Only: item control page