fulltext.study @t Gmail

Structural and electronic characterization of a Fridericia heliota luciferin-related derivative, based on quantum chemistry

Paper ID Volume ID Publish Year Pages File Format Full-Text
26542 43961 2014 9 PDF Available
Title
Structural and electronic characterization of a Fridericia heliota luciferin-related derivative, based on quantum chemistry
Abstract

•A natural luciferin-analog was structurally and electronically characterized.•CompX equilibria consist of six species due to dissociation and tautomerism reactions.•The properties of this molecule are governed by a strong OH⋯H ionic bond.•The large Stoke shift was explained by a enol → keto phototautomerization.

CompX is a natural analog of the unknown luciferin of the bioluminescence earthworm Fridericia heliota. Given the difficulties of characterizing luciferin, the objective of this work was the quantum chemistry based structural and electronic characterization of CompX. A main feature of this molecule is a strong partially covalent OH⋯O ionic bond, with sigma bonding character, present in all CompX species. Atomic charge transfers involving this interaction determine the relative stability of all species. Moreover, this interaction is involved in an excited state intramolecular proton transfer leading to a phototautomerism reaction. Thus, the large Stokes shift observed for CompX is attributed to an enol → keto photoconversion.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Fridericia heliota; Phototautomerism; CompX; Quantum theory of atoms in molecules; Bioluminescence; Excited state intramolecular proton transfer
First Page Preview
Structural and electronic characterization of a Fridericia heliota luciferin-related derivative, based on quantum chemistry
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 288, 15 August 2014, Pages 46–54
Authors
, ,
Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us