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Conformational properties and photochemistry of new allyl tetrazoles: Matrix isolation FTIR and computational approach

Paper ID Volume ID Publish Year Pages File Format Full-Text
26164 43937 2013 10 PDF Available
Title
Conformational properties and photochemistry of new allyl tetrazoles: Matrix isolation FTIR and computational approach
Abstract

The photochemistry and molecular structure of 1-allyltetrazole (1-ALT) and 2-allyltetrazole (2-ALT) were studied in argon matrices by infrared spectroscopy and B3LYP/6-311++G(2d,2p) calculations. Both allyltetrazoles were found to possess three stable conformers (1-ALT1, 1-ALT2, 1-ALT3 and 2-ALT1, 2-ALT2, 2-ALT3) differing in the orientation of the allyl group relative to the ring. Matrix isolation technique together with the annealing experiments allowed for detection of all 1-ALT and 2-ALT conformers. A conformational cooling phenomenon was observed for the 1-ALT3 → 1-ALT1 process in agreement with the predicted low energy barrier of 4.84 kJ mol−1 for this reaction. The broad-band UV irradiation of 1-ALT/Ar and 2-ALT/Ar matrices led to the same photoproducts. The main product N-allylcarbodiimide (P1) and two minor photoproducts allylcyanamide (P2) and C-allylnitrilimine (P3) are formed through the tetrazole ring cleavage and N2 elimination. None of these molecules have been described before.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Theoretical and spectroscopic characterization of allyl tetrazoles. ► Three conformers of 1-ALT and 2-ALT trapped in solid argon environment. ► Conformational cooling phenomenon for 1-ALT3 → 1-ALT1. ► N-allylcarbodiimide molecule as the main product of allyl tetrazoles photolysis.

Keywords
Allylcarbodiimide; DFT; Conformational cooling; Allylcyanamide
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Conformational properties and photochemistry of new allyl tetrazoles: Matrix isolation FTIR and computational approach
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 251, 1 January 2013, Pages 118–127
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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