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Molecules 2018, 23(1), 128; https://doi.org/10.3390/molecules23010128

How and How Much Molecular Conformation Affects Electronic Circular Dichroism: The Case of 1,1-Diarylcarbinols

1
Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
2
Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy
*
Author to whom correspondence should be addressed.
Received: 12 December 2017 / Revised: 29 December 2017 / Accepted: 8 January 2018 / Published: 9 January 2018
(This article belongs to the Section Analytical Chemistry)
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Abstract

Chiroptical spectra such as electronic circular dichroism (ECD) are said to be much more sensitive to conformation than their non-chiroptical counterparts, however, it is difficult to demonstrate such a common notion in a clear-cut way. We run DFT and TDDFT calculations on two closely related 1,1-diarylmethanols which show mirror-image ECD spectra for the same absolute configuration. We demonstrate that the main reason for the different chiroptical response of the two compounds lies in different conformational ensembles, caused by a single hydrogen-to-methyl substitution. We conclude that two compounds, having the same configuration but different conformation, may exhibit mirror-image ECD signals, stressing the importance and impact of conformational factors on ECD spectra. View Full-Text
Keywords: stereochemistry; conformational analysis; absolute configuration; electronic circular dichroism calculations; vibronic circular dichroism; benzene sector rules stereochemistry; conformational analysis; absolute configuration; electronic circular dichroism calculations; vibronic circular dichroism; benzene sector rules
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Padula, D.; Pescitelli, G. How and How Much Molecular Conformation Affects Electronic Circular Dichroism: The Case of 1,1-Diarylcarbinols. Molecules 2018, 23, 128.

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