Racemization barriers of atropisomeric 3,3′-bipyrroles

An experimental study with theoretical verification

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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)71245-71249
Number of pages5
JournalRSC Advances
Volume6
Issue number75
DOIs
StatePublished - 2016

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Carbon
Circular dichroism spectroscopy
Energy barriers
Derivatives

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Chatterjee, S., Butterfoss, G., Mandal, M., Paul, B., Gupta, S., Bonneau, R., & Jaisankar, P. (2016). Racemization barriers of atropisomeric 3,3′-bipyrroles: An experimental study with theoretical verification. RSC Advances, 6(75), 71245-71249. https://doi.org/10.1039/c6ra07585a

Racemization barriers of atropisomeric 3,3′-bipyrroles : An experimental study with theoretical verification. / Chatterjee, Sourav; Butterfoss, Glenn; Mandal, Madhumita; Paul, Bishwajit; Gupta, Sreya; Bonneau, Richard; Jaisankar, Parasuraman.

In: RSC Advances, Vol. 6, No. 75, 2016, p. 71245-71249.

Research output: Contribution to journalArticle

Chatterjee, S, Butterfoss, G, Mandal, M, Paul, B, Gupta, S, Bonneau, R & Jaisankar, P 2016, 'Racemization barriers of atropisomeric 3,3′-bipyrroles: An experimental study with theoretical verification', RSC Advances, vol. 6, no. 75, pp. 71245-71249. https://doi.org/10.1039/c6ra07585a
Chatterjee, Sourav ; Butterfoss, Glenn ; Mandal, Madhumita ; Paul, Bishwajit ; Gupta, Sreya ; Bonneau, Richard ; Jaisankar, Parasuraman. / Racemization barriers of atropisomeric 3,3′-bipyrroles : An experimental study with theoretical verification. In: RSC Advances. 2016 ; Vol. 6, No. 75. pp. 71245-71249.
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