Document Detail

Regiochemical Substituent Switching of Spin States in Aryl(trifluoromethyl)carbenes.
MedLine Citation:
PMID:  22066830     Owner:  NLM     Status:  Publisher    
Although aryl(trifluoromethyl)diazirines have achieved great popularity in photoaffinity labeling applications, the prop-erties of the corresponding carbenes have not been as widely explored. Here, low-temperature matrix isolation spectroscopy and reactivity indicate that, in contrast to meta-methoxyphenyl(trifluoromethyl)carbene and most known aryl(CF3)carbenes, the para-isomer is a ground-state singlet rather than triplet. DFT calculations support these results, as well as the notion that the p-CH3O group stabilizes the singlet carbene via resonance. These results may have relevance to the wide range of substituted aryl(CF3)diazirines in photoaffinity applications.
Myoung-Geun Song; Robert Stuart Sheridan
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-11-8
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  -     ISSN:  1520-5126     ISO Abbreviation:  -     Publication Date:  2011 Nov 
Date Detail:
Created Date:  2011-11-9     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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