1996
DOI: 10.1002/anie.199608701
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The First C2‐Symmetric, Chiral Monomethine Dye—An Apparent Violation of the Helicity Rule for Optical Rotation

Abstract: COMMUNICATIONSisotropicallq. No ;ittempt was made to locate hydrogen atoms. The final cycle of full-matrix least-squares refinement was converged with R = x(lF,ll.FLF,i)/ Zlk;l = 0.056 and R = [xir([Fol -~F ,~) z /~~r~F ,~' ] i ' 2 = 0.063. The first five residual peaks in the final difference F-map are ghosts of heavy atoms [16]

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Cited by 20 publications
(9 citation statements)
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“…3 For 3 the corresponding value obtained from temperature dependent 1 H NMR spectroscopy is 2.5 kJ/mol. 6 We can therefore state that, within the accuracy of experimental data, the effect of the two chiral substituents is less than additive and certainly not synergistic, which is not surprising if one considers the mechanism by which the chiral discrimination comes about.…”
Section: Spectroscopy Monomethinium Dyementioning
confidence: 99%
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“…3 For 3 the corresponding value obtained from temperature dependent 1 H NMR spectroscopy is 2.5 kJ/mol. 6 We can therefore state that, within the accuracy of experimental data, the effect of the two chiral substituents is less than additive and certainly not synergistic, which is not surprising if one considers the mechanism by which the chiral discrimination comes about.…”
Section: Spectroscopy Monomethinium Dyementioning
confidence: 99%
“…The starting geometry for P-helical 2 was the known X-ray structure; 3 for the M-helical diastereomer the mirrorimage was generated except for the two stereogenic centers, which were both kept in their R-configurations. For the trimethinium dye 11, we started with the known X-ray structure of the achiral congener 13, 7 for 14, the optimized structure of 11 was lengthened by two symmetrically placed C-H-units and reoptimized.…”
Section: Computationsmentioning
confidence: 99%
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“…However, in order to effect chiral discrimination, i.e., make the P-and the M-helically twisted forms chemically different, chiral substitutents were introduced into the indolyl end groups. 9,10 …”
mentioning
confidence: 99%