eprintid: 20473
rev_number: 12
userid: 1419
dir: disk0/00/02/04/73
datestamp: 2014-02-13 19:17:52
lastmod: 2017-10-30 23:57:45
status_changed: 2014-02-13 19:17:52
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Specht, KM
creators_name: Nam, J
creators_name: Ho, DM
creators_name: Berova, N
creators_name: Kondru, RK
creators_name: Beratan, DN
creators_name: Wipf, P
creators_name: Pascal, JA
creators_name: Kahne, D
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creators_email: pwipf@pitt.edu
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creators_id: PWIPF
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title: Determining absolute configuration in flexible molecules: A case study
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: 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.
date: 2001-09-19
date_type: published
publication: Journal of the American Chemical Society
volume: 123
number: 37
pagerange: 8961 - 8966
refereed: TRUE
issn: 0002-7863
id_number: 10.1021/ja0104406
pmid: 11552802
mesh_headings: Benzoates--chemistry
mesh_headings: Circular Dichroism
mesh_headings: Crystallography, X-Ray
mesh_headings: Molecular Conformation
mesh_headings: Naphthalenes--chemistry
mesh_headings: Optical Rotatory Dispersion--methods
mesh_headings: Solutions
mesh_headings: Stereoisomerism
mesh_headings: Thermodynamics
chemical_names: Benzoates
chemical_names: Naphthalenes
chemical_names: Solutions
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/20473/1/licence.txt