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Circular dichroism spectroscopy of 2‐aminotetralins
Author(s) -
Jansen Johanna M.,
Johansson Anette M.,
Karlén Anders,
Hacksell Uli
Publication year - 1995
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.530070206
Subject(s) - chemistry , tetralin , circular dichroism , cotton effect , substituent , stereochemistry , moiety , absolute configuration , sign (mathematics) , spectroscopy , organic chemistry , mathematical analysis , physics , mathematics , quantum mechanics , catalysis
The circular dichroism (CD) spectra of a series of oxygenated 2‐(dipropylamino)tetralin derivatives are reported. On the basis of known absolute configurations and conformational preferences of the compounds, the validity of published correlations between the sign of the 1 L b Cotton effect and the three‐dimensional structure was examined. Contrary to predictions, substitution in position 6 or 7 of the tetralin moiety did not change the sign of the 1 L b Cotton effect. An unexpected sign inversion was, however, observed in some of the compounds containing methyl substituents in the nonaromatic ring. The occurrence of this inversion was not correlated with a change in conformational behaviour and varied depending on the position and nature of the aromatic substituent. No correlations were obvious between the sign of the 1 L b Cotton effect and the absolute configuration and conformational preferences of the compounds. Therefore, at present, CD spectroscopy does not appear to be useful in assignments of the absolute configurations of 2‐(dipropylamino)tetralin derivatives. © 1995 Wiley‐Liss, Inc.