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Chiroptical Properties of Streptorubin B: The Synergy Between Theory and Experiment
Author(s) -
Andrade Marta S.,
Silva Vanessa S.,
Lourenço Ana M.,
Lobo Ana M.,
Rzepa Henry S.
Publication year - 2015
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.22486
Subject(s) - chemistry , atropisomer , circular dichroism , vibrational circular dichroism , optical rotation , polarizability , population , raman optical activity , crystallography , chirality (physics) , stereochemistry , computational chemistry , organic chemistry , molecule , nambu–jona lasinio model , demography , chiral symmetry breaking , physics , quantum mechanics , sociology , quark
Analysis of the calculated and measured optical rotation (OR) together with other calculated chiroptical properties such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of the prodigiosin alkaloid streptorubin B shows that these are dominated by the pseudoenantiomeric atropisomers anti ‐( S )‐streptorubin B ( 1A ) and syn ‐( S )‐streptorubin ( 1B ). Atropisomerism is a dynamic phenomenon with a potentially nonequilibrium population of isomers, and accordingly the measured chiroptical responses may vary with time, concentration, temperature, and the anion of the salts used. Streptorubin also has the potential to form stacked homodimers for which the optical rotations measured at 589 nm can vary greatly due to the presence of ECD‐active electronic transitions in this region. Chirality 27:745–751, 2015 . © 2015 Wiley Periodicals, Inc.