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Aryl-Csp<sup>3</sup> bond rotation barriers of 2-aryl perhydropyrrolo[3,4- c]pyrrole-1,3-diones

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:
CreatorsEmailPitt UsernameORCID
Damodaran, K
Nielsen, SD
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Zhang, W
Lu, Y
Curran, DPcurran@pitt.eduCURRAN
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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