Racemization barriers of atropisomeric 3,3′-bipyrroles: An experimental study with theoretical verification

Sourav Chatterjee; Glenn L. Butterfoss; Madhumita Mandal; Bishwajit Paul; Sreya Gupta; Richard Bonneau; Parasuraman Jaisankar

doi:10.1039/c6ra07585a

Racemization barriers of atropisomeric 3,3′-bipyrroles: An experimental study with theoretical verification

Sourav Chatterjee, Glenn L. Butterfoss, Madhumita Mandal, Bishwajit Paul, Sreya Gupta, Richard Bonneau, Parasuraman Jaisankar

Research output: Contribution to journal › Article › peer-review

Abstract

The significant rotational energy barrier about the stereogenic carbon-carbon bond of axially chiral 3,3′-bipyrroles has been investigated by electronic circular dichroism (ECD) spectroscopy, time dependent HPLC analysis, and computational modeling. The results elucidate pathways and transition states involved in configurational inversion, thereby confirming that 3,3′-bipyrrole derivatives can exist in stable and isolable atropisomeric forms.

Original language	English (US)
Pages (from-to)	71245-71249
Number of pages	5
Journal	RSC Advances
Volume	6
Issue number	75
DOIs	https://doi.org/10.1039/c6ra07585a
State	Published - 2016

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1039/c6ra07585a

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abstract = "The significant rotational energy barrier about the stereogenic carbon-carbon bond of axially chiral 3,3′-bipyrroles has been investigated by electronic circular dichroism (ECD) spectroscopy, time dependent HPLC analysis, and computational modeling. The results elucidate pathways and transition states involved in configurational inversion, thereby confirming that 3,3′-bipyrrole derivatives can exist in stable and isolable atropisomeric forms.",

author = "Sourav Chatterjee and Butterfoss, {Glenn L.} and Madhumita Mandal and Bishwajit Paul and Sreya Gupta and Richard Bonneau and Parasuraman Jaisankar",

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AU - Chatterjee, Sourav

AU - Butterfoss, Glenn L.

AU - Mandal, Madhumita

AU - Paul, Bishwajit

AU - Gupta, Sreya

AU - Bonneau, Richard

AU - Jaisankar, Parasuraman

PY - 2016

Y1 - 2016

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AB - The significant rotational energy barrier about the stereogenic carbon-carbon bond of axially chiral 3,3′-bipyrroles has been investigated by electronic circular dichroism (ECD) spectroscopy, time dependent HPLC analysis, and computational modeling. The results elucidate pathways and transition states involved in configurational inversion, thereby confirming that 3,3′-bipyrrole derivatives can exist in stable and isolable atropisomeric forms.

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Racemization barriers of atropisomeric 3,3′-bipyrroles: An experimental study with theoretical verification

Abstract

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