NDLI: Isocyano compounds newly recognized in photochemical reaction of thiazole: matrix-isolation FT-IR and theoretical studies

Content Provider	Royal Society of Chemistry (RSC)
Author	Miyazaki, Jun Nakata, Munetaka Takiyama, Hiroshi
Copyright Year	2017
Abstract	UV-induced photoreactions of thiazole isolated in low-temperature argon matrices have been investigated by a joint use of infrared spectroscopy and density-functional-theory calculations. Photoproducts have been identified by comparison of the observed infrared spectra with the corresponding calculated spectral patterns, leading to the conclusion that undetected open-chain molecules, syn-2-isocyanoethenethiol (CN–CHCH–SH) and 2-isocyanothiirane, are initially produced by cleavage of the CS–CN bond with hydrogen-atom migration, when the matrix samples are exposed to UV radiation coming from a super high-pressure mercury lamp for 3 min. In the secondary photolysis, syn-2-isocyanoethenethiol and 2-isocyanothiirane change to another unknown molecule, 2-isocyanoethanethial (CN–CH2–CHS), by hydrogen-atom migration with generation of the CS double bond. These photoreaction pathways are supported by kinetic analysis of the absorbance changes of IR bands against irradiation time. We have also found that HCN and the ˙CHCH–S˙ biradical are photodecomposed from thiazole by cleavage of the CN–CC bond following the cleavage of the CS–CN bond, where the hydrogen atom on the center carbon atom of ˙CHCH–S˙ immediately migrates to the end carbon atom to form CH2CS or to the sulfur atom to form HCC–SH. In addition, weak bands of the species of interest in astrophysics and astrochemistry such as HCCH, NC–SH, HNCS, HCNS, and the ˙CN radical are detected, but the photoconversion from thiazole to isothiazole or Dewar thiazole is not found. The ring-opening photoreaction, photoisomerization and photodecomposition pathways of thiazole isolated in low-temperature argon matrices are discussed comprehensively.
Starting Page	4960
Ending Page	4974
Page Count	15
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	7
Issue Number	9
Journal	RSC Advances
DOI	10.1039/c6ra27496j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Infrared spectroscopy Non-Kekulé molecule Hydrogen Photoisomerization HCC Photodissociation Carbon Isothiazole Covalent bond Mercury-vapor lamp Astrochemistry Argon Sulfur Thiazole
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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