Combined use of three forms of chiroptical spectroscopies in the study of the absolute configuration and conformational properties of 3-phenylcyclopentanone, 3-phenylcyclohexanone, and 3-phenylcycloheptanone

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F13%3A00421994" target="_blank" >RIV/61388963:_____/13:00421994 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.tet.2013.10.016" target="_blank" >http://dx.doi.org/10.1016/j.tet.2013.10.016</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2013.10.016" target="_blank" >10.1016/j.tet.2013.10.016</a>

Result language

angličtina

Original language name

Combined use of three forms of chiroptical spectroscopies in the study of the absolute configuration and conformational properties of 3-phenylcyclopentanone, 3-phenylcyclohexanone, and 3-phenylcycloheptanone

Original language description

Three forms of chiroptical spectroscopies, electronic circular dichroism (ECD), vibrational circular dichroism (VCD), and optical rotatory dispersion (ORD) have been employed to study the configuration and conformational properties of the three molecules: (S)-3-phenylcyclopentanone, (S)-3phenylcyclohexanone, and (S)-3-phenylcycloheptanone (including (S)-3-phenylcyclopentanone-2,2,5,5d(4) and (S)-3-phenylcyclohexanone-2,2,6,6-d(4)). ECD and VCD spectra in the mid-IR for the three molecular systems are marginally dependent on fine conformational details, as interpreted in terms of standard DFT computational methods, with common spectroscopic features to the three systems clearly identified. Accounting for vibronic coupling mechanisms reproduces the structuring of ECD n ->pi* band. The ORD curves are quite similar for the three types of molecules, but their interpretation highlights a crucial role played by conformations of the cycloalkanone ring in the case of (S)-3phenylcycloheptanone.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2013

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Tetrahedron

ISSN

0040-4020

e-ISSN

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Volume of the periodical

69

Issue of the periodical within the volume

50

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

10752-10762

UT code for WoS article

000327692000008

EID of the result in the Scopus database

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