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Quantum‐chemical calculations on the electronic circular dichroism of (−)‐dibromophakellin and (−)‐dibromophakell‐statin
Author(s) -
Atodiresei Iuliana,
Zöllinger Michael,
Lindel Thomas,
Fleischhauer Jörg,
Raabe Gerhard
Publication year - 2007
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.20388
Subject(s) - chemistry , circular dichroism , chirality (physics) , quantum chemical , density functional theory , methanol , computational chemistry , spectral line , imidazole , solvent , vibrational circular dichroism , molecule , stereochemistry , organic chemistry , quantum mechanics , chiral symmetry , physics , nambu–jona lasinio model , quark
The CD spectra of the pyrrole‐imidazole alkaloids, (−)‐dibromophakellin and (−)‐dibromophakellstatin, have been calculated employing the quantum‐chemical time‐dependent density functional theory. Comparison of calculated and measured spectra showed that this well‐established method is also a useful tool to elucidate the absolute stereochemistry of this class of compounds. The computational results have further been used to analyze the spectra measured in methanol and to explain the remarkable red shift of one CD band when trifluoroethanol is used as a solvent instead of methanol. Chirality, 2007. © 2007 Wiley‐Liss, Inc.