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Structural and Conformational Dependence of Optical Rotation Angles

Kondru, RK and Wipf, P and Beratan, DN (1999) Structural and Conformational Dependence of Optical Rotation Angles. Journal of Physical Chemistry A, 103 (33). 6603 - 6611. ISSN 1089-5639

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The ability to compute and to interpret optical rotation angles of chiral molecules is of great value in assigning relative and absolute stereochemistry. The molar rotations for an indoline and an azetidine, as well as for menthol and menthone, were calculated using ab inito methods and compared to the experimental values. In one case the calculated rotation angle allowed the assignment of the absolute configuration of a heterocycle of unknown stereochemistry. The critical importance of Boltzmann averaging of conformers for reliable prediction of the optical rotation angle was established. Comparisons between static-field and time-dependent methods were made pointing to the limits and validity of the methods as electronic resonance is approached. A protocol analogous to population analysis was used to analyze atomic contributions to the rotation angle in specific conformers. The combination of atomic contribution maps and conformational analysis may provide an indirect tool to assist in three-dimensional structure determination.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Kondru, RK
Wipf, Ppwipf@pitt.eduPWIPF
Beratan, DN
Date: 19 August 1999
Date Type: Publication
Journal or Publication Title: Journal of Physical Chemistry A
Volume: 103
Number: 33
Page Range: 6603 - 6611
DOI or Unique Handle: 10.1021/jp990697e
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1089-5639
Date Deposited: 22 Jul 2015 14:51
Last Modified: 02 Feb 2019 15:56


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