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Chiral Sulfur Compounds Studied by Raman Optical Activity: tert ‐Butanesulfinamide and its Precursor tert ‐Butyl tert ‐Butanethiosulfinate
Author(s) -
Qiu Shi,
Li Guanna,
Lu Shengmei,
Huang Baokun,
Feng Zhaochi,
Li Can
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22038
Subject(s) - chemistry , raman optical activity , raman spectroscopy , sulfur , medicinal chemistry , chirality (physics) , organic chemistry , stereochemistry , computational chemistry , molecule , chiral symmetry , optics , quantum mechanics , physics , nambu–jona lasinio model , quark
Two chiral sulfur compounds, tert ‐butyl tert ‐butanethiosulfinate ( 1 ) and tert ‐butanesulfinamide ( 2 ), with inversion of configuration, have been studied by Raman optical activity (ROA) and electronic circular dichroism combined with density functional theory calculation. With the S–S linkage in 1 , the couplings between the two tertiary carbon atoms often generate large ROA signals, whereas the tertiary carbon atom itself generally makes a large contribution to ROA signals in 2 for similar vibrational modes. The conformational dependence of ROA parameters provides probing conformation around the S–S bond from a new perspective. The simultaneous use of electronic circular dichroism and ROA is warranted to extract reliable conformational information. ROA provides a suitable candidate for the stereochemical study of chiral sulfur compounds, especially its capability of sensing the conformation around the S–S bond. Chirality 24:731–740, 2012. © 2012 Wiley Periodicals, Inc.