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Determining absolute configuration in flexible molecules: A case study

Specht, KM and Nam, J and Ho, DM and Berova, N and Kondru, RK and Beratan, DN and Wipf, P and Pascal, JA and Kahne, D (2001) Determining absolute configuration in flexible molecules: A case study. Journal of the American Chemical Society, 123 (37). 8961 - 8966. ISSN 0002-7863

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Assigning absolute configuration of molecules continues to be a major problem. Determining absolute configuration in conformationally flexible systems is challenging, even for experts. Here, we present a case study in which we use a combination of molecular modeling, solution NMR, and X-ray crystallography to illustrate why it is difficult to use solution methods alone for configuration assignment. For the case examined, a comparison of calculated and experimental optical rotatory dispersion (ORD) data provides the most straightforward way to assign the absolute configuration.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Specht, KM
Nam, J
Ho, DM
Berova, N
Kondru, RK
Beratan, DN
Wipf, Ppwipf@pitt.eduPWIPF
Pascal, JA
Kahne, D
Date: 19 September 2001
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 123
Number: 37
Page Range: 8961 - 8966
DOI or Unique Handle: 10.1021/ja0104406
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Benzoates--chemistry; Circular Dichroism; Crystallography, X-Ray; Molecular Conformation; Naphthalenes--chemistry; Optical Rotatory Dispersion--methods; Solutions; Stereoisomerism; Thermodynamics
PubMed ID: 11552802
Date Deposited: 13 Feb 2014 19:17
Last Modified: 30 Oct 2017 23:57


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