Damodaran, K and Nielsen, SD and Geib, SJ and Zhang, W and Lu, Y and Curran, DP
(2009)
Aryl-Csp<sup>3</sup> bond rotation barriers of 2-aryl perhydropyrrolo[3,4- c]pyrrole-1,3-diones.
Journal of Organic Chemistry, 74 (15).
5481 - 5485.
ISSN 0022-3263
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Abstract
(Chemical Equation Presented) The static and dynamic features of 2-aryl perhydropyrrolo[3,4-c]pyrrole-1,3-diones bearing N-acyl substituents have been assessed with the aid of crystal structures and VT NMR spectra. Rotation barriers for the aryl-Csp3 bonds in these molecules show surprising variation. Amide-substituted derivatives and fused piperazinediones (six-membered fusion) exhibit very substantial barriers of 14-15 kcal/mol. Fused benzodiazepinediones (seven-membered fusion) have lower but still significant barriers (10 kcal/mol), while fused hydantoins (five-membered fusion) have barriers that are too low to measure by VT NMR (≤10 kcal/mol). A rationale for the origin of the barriers is presented. © 2009 American Chemical Society.
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Details
Item Type: |
Article
|
Status: |
Published |
Creators/Authors: |
|
Date: |
7 August 2009 |
Date Type: |
Publication |
Journal or Publication Title: |
Journal of Organic Chemistry |
Volume: |
74 |
Number: |
15 |
Page Range: |
5481 - 5485 |
DOI or Unique Handle: |
10.1021/jo901123c |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
0022-3263 |
MeSH Headings: |
Crystallography, X-Ray; Models, Molecular; Molecular Conformation; Pyrroles--chemistry; Rotation; Stereoisomerism; Thermodynamics |
PubMed ID: |
19572578 |
Date Deposited: |
18 Feb 2013 15:33 |
Last Modified: |
22 Jun 2021 12:56 |
URI: |
http://d-scholarship.pitt.edu/id/eprint/17333 |
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