cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions

Banerjee, S and Tumminakatti, S and Ghosh, S and Voora, VK and Prabhakaran, EN (2024) cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions. In: Organic and Biomolecular Chemistry .

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Abstract

NMR spectral and theoretical analyses of homologous prolyl carbamates reveal subtle charge transfer tetrel bonding interactions (TBIs), selectively stabilizing their cisPro rotamers. These TBIs involve C-terminal-amide to N-terminal carbamate carbonyl-carbonyl (n � �* type) followed by intra-carbamate (n � �* type) charge transfer interactions exclusively in the cisPro motif. The number of TBIs and hence the cisPro stability increase with increasing number of Cβ groups at the carbamate alcohol. Increasing solvent polarities also increase the relative cisPro carbamate stabilities. © 2024 The Royal Society of Chemistry.

Item Type:	Journal Article
Publication:	Organic and Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
Additional Information:	The copyright for this article belongs to the Publisher.
Keywords:	Bonding interactions; Carbamate stability; Charge transfer interaction; N-terminals; Rotamers; Solvent polarity; Tetrels; carbonyl; �-type, Charge transfer
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	22 Nov 2024 20:44
Last Modified:	22 Nov 2024 20:44
URI:	http://eprints.iisc.ac.in/id/eprint/86841

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