Kondru, RK and Beratan, DN and Friestad, GK and Smith, AB and Wipf, P
(2000)
Chiral Action at a Distance: Remote Substituent Effects on the Optical Activity of Calyculins A and B.
Organic Letters, 2 (11).
1509 - 1512.
ISSN 1523-7060
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Abstract
(Equation Presented) Calyculins A and B differ only by the (E)- vs (Z)-configuration at C(2). Yet, they show a large difference in optical rotations. We demonstrate a new strategy that provides a physical analysis of this long-range chiro-optical effect by Boltzmann-averaged atomic contribution mapping. The polarizability characteristics of the CN substituent rather than the perturbation of the stereogenic centers or the introduction of dissymmetry into the polyene chain give rise to the remarkable difference in rotation angles.
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Details
Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Kondru, RK | | | | Beratan, DN | | | | Friestad, GK | | | | Smith, AB | | | | Wipf, P | pwipf@pitt.edu | PWIPF | |
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Date: |
1 June 2000 |
Date Type: |
Publication |
Journal or Publication Title: |
Organic Letters |
Volume: |
2 |
Number: |
11 |
Page Range: |
1509 - 1512 |
DOI or Unique Handle: |
10.1021/ol005634p |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
1523-7060 |
MeSH Headings: |
Biological Factors--chemistry; Carcinogens--chemistry; Enzyme Inhibitors--chemistry; Models, Molecular; Molecular Conformation; Optical Rotation; Organophosphates--chemistry; Oxazoles--chemistry; Phosphoprotein Phosphatases--antagonists & inhibitors; Stereoisomerism; Thermodynamics; Vasoconstrictor Agents--chemistry |
PubMed ID: |
10841466 |
Date Deposited: |
21 Feb 2014 21:09 |
Last Modified: |
02 Aug 2020 13:57 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/20546 |
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