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Open AccessArticle

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.
Molecules 2018, 23(1), 128; https://doi.org/10.3390/molecules23010128
Received: 12 December 2017 / Revised: 29 December 2017 / Accepted: 8 January 2018 / Published: 9 January 2018
(This article belongs to the Section Analytical Chemistry)
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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MDPI and ACS Style

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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