The DOI matches its Crossref record; 13 of the 13 references it cites were found in a registry or an index.
The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy
Abstract
The vibrational circular dichroism (VCD) spectra of the two enantiomers of a chiral molecule are of equal magnitude and opposite sign: i.e. mirror‐image enantiomers give mirror‐image VCD spectra. In principle, the absolute configuration (AC) of a chiral molecule can therefore be determined from its VCD spectrum. In practice, the determination of the AC of a chiral molecule from its experimental VCD spectrum requires a methodology which reliably predicts the VCD spectra of its enantiomers. The only reliable methodology developed to date uses the Stephens quantum‐mechanical theory of the rotational strengths of fundamental vibrational transitions, developed in the early 1980s, implemented using ab initio density functional theory in the GAUSSIAN program in the mid 1990s. This methodology has by now been widely used in determining ACs from experimental VCD spectra. In this article we discuss the protocol for determining the ACs of chiral molecules with optimum reliability and its implementation for a variety of molecules, including the D 3 symmetry perhydrotriphenylene, a thiazino‐oxadiazolone recently shown to be a highly active calcium entry channel blocker, the alkaloid natural products schizozygine, iso‐schizogaline, and iso‐schizogamine, and the iridoid natural products plumericin, iso‐plumericin, and prismatomerin. The power of VCD spectroscopy in determining ACs, even for large organic molecules and for substantially conformationally‐flexible organic molecules is clearly documented. Chirality, 2008. © 2007 Wiley‐Liss, Inc.
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Cites
Stephens, P. J., Devlin, F. J., Chabalowski, C. F., & Frisch, M. J. (1994) · The Journal of Physical Chemistry · doi:10.1021/j100096a001 · Cited by 23,248
Self-citationCircular Dichroism: Principles and Applications
Berova, N. D., 中西, 香., & Woody, R. W. (1994) · Cited by 1,264
Cheeseman, J. R., Frisch, M. J., Devlin, F. J., & Stephens, P. J. (1996) · Chemical Physics Letters · doi:10.1016/0009-2614(96)00154-6 · Cited by 454
Self-citationVibrational circular dichroism
Nafie, L. A., Keiderling, T. A., & Stephens, P. J. (1976) · Journal of the American Chemical Society · doi:10.1021/ja00426a007 · Cited by 419
Self-citationDevlin, F. J., Finley, J. W., Stephens, P. J., & Frisch, M. J. (1995) · The Journal of Physical Chemistry · doi:10.1021/j100046a014 · Cited by 333
Self-citationTheoretical calculation of vibrational circular dichroism spectra
Stephens, P. J., Devlin, F. J., Ashvar, C. S., Chabalowski, C. F., & Frisch, M. J. (1994) · Faraday Discussions · doi:10.1039/fd9949900103 · Cited by 187
Self-citationDevlin, F. J., Stephens, P. J., Cheeseman, J. R., & Frisch, M. J. (1997) · The Journal of Physical Chemistry A · doi:10.1021/jp971905a · Cited by 158
Self-citationStephens, P. J., Devlin, F. J., Gasparrini, F., et al. (2007) · The Journal of Organic Chemistry · doi:10.1021/jo070302k · Cited by 116
Self-citationDevlin, F. J., Stephens, P. J., Cheeseman, J. R., & Frisch, M. J. (1997) · The Journal of Physical Chemistry A · doi:10.1021/jp9712359 · Cited by 114
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Calcaterra, A., & D’Acquarica, I. (2018) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/j.jpba.2017.07.008 · Cited by 481
Luminescent chiral lanthanide(iii) complexes as potential molecular probes
Muller, G. (2009) · Dalton Transactions · doi:10.1039/b909430j · Cited by 364
Buhse, T., Cruz, J.-M., Noble-Terán, M. E., Hochberg, D., Ribó, J. M., Crusats, J., & Micheau, J.-C. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00819 · Cited by 189
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Metadata
- Authors
- Stephens, P. J., Devlin, F. J., & Pan, J.
- Venue
- Chirality
- Publisher
- Wiley
- Published
- 2007-10-22
- Volume
- 20
- Issue
- 5
- Pages
- 643-663
- ISSN
- 0899-0042 (ISSN-L)
- 1520-636X
- OpenAlex
- W1966519714
- Cited by
- 366
- References
- 13
- FWCI
- 9.59
- Type
- journal article
- Language
- en
- Open access
- closed
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