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Keywords:

  • chiral discrimination;
  • chiral recognition;
  • local vibrational modes;
  • H-bonding;
  • chirodiastaltic energy;
  • decomposition of normal modes

ABSTRACT

Chiral discrimination of homochiral and heterochiral H-bonded complexes is a challenge for both experimentalists and computational chemists. It is demonstrated that a two-pronged approach based on far-infrared vibrational spectroscopy and the calculation of local mode frequencies facilitates the chiral discrimination of H-bonded dimers. The local H-bond stretching frequencies identify the strongest H-bonds and by this the dominating chiral diastereomer. This is shown in the case of peroxide, trioxide, hydrazine, glycidol, and butan-2-ol dimers as well as propylene oxideglycidol complexes investigated with the help of second-order Møller–Plesset perturbation, coupled cluster, and density functional theory calculations where, in the latter case, the ωB97X-D functional was used for an improved description of H-bonding. In some cases, additional intermolecular interactions overrule the important role of H-bonding, which is found by calculating chirodiastaltic energies. Chirality 25:185–196, 2013. © 2013 Wiley Periodicals, Inc.

Featured Compounds

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  1. 1 - 26
Compound 1a
Molecular Weight:68.0294
Molecular Formula:H4O4
InChIKey:MMBMIVSDYYPRHH-UHFFFAOYSA-N
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Compound 1b
Molecular Weight:68.0294
Molecular Formula:H4O4
InChIKey:MMBMIVSDYYPRHH-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:100.0282
Molecular Formula:H4O6
InChIKey:NOSFEYGILDWYAM-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:100.0282
Molecular Formula:H4O6
InChIKey:NOSFEYGILDWYAM-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:64.0903
Molecular Formula:H8N4
InChIKey:NOVHEGOWZNFVGT-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:64.0903
Molecular Formula:H8N4
InChIKey:NOVHEGOWZNFVGT-UHFFFAOYSA-N
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Compound 4a
Molecular Weight:100.0712
Molecular Formula:F2H6N4
InChIKey:VGSMFTRNGCPAJH-UHFFFAOYSA-N
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Compound 4b
Molecular Weight:100.0712
Molecular Formula:F2H6N4
InChIKey:VGSMFTRNGCPAJH-UHFFFAOYSA-N
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Compound 5a
Molecular Weight:104.0103
Molecular Formula:F2H2O4
InChIKey:FBRMJEVAHFDEKF-UHFFFAOYSA-N
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Compound 5b
Molecular Weight:104.0103
Molecular Formula:F2H2O4
InChIKey:FBRMJEVAHFDEKF-UHFFFAOYSA-N
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Compound 6a
Molecular Weight:136.0091
Molecular Formula:F2H2O6
InChIKey:PBSZRUTWMLABOW-UHFFFAOYSA-N
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Compound 6b
Molecular Weight:136.0091
Molecular Formula:F2H2O6
InChIKey:PBSZRUTWMLABOW-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:148.1571
Molecular Formula:C6H12O4
InChIKey:JPMDGKVQJJAWMT-RUCXOUQFSA-N
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Compound 7b
Molecular Weight:148.1571
Molecular Formula:C6H12O4
InChIKey:JPMDGKVQJJAWMT-OASOTCBPSA-N
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Compound 8a
Molecular Weight:148.2432
Molecular Formula:C8H20O2
InChIKey:GKMQWTVAAMITHR-DGPROHSZSA-N
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Compound 8b
Molecular Weight:148.2432
Molecular Formula:C8H20O2
InChIKey:GKMQWTVAAMITHR-KRSQWWHXSA-N
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Compound 9a
Molecular Weight:148.2432
Molecular Formula:C8H20O2
InChIKey:GKMQWTVAAMITHR-DGPROHSZSA-N
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Compound 9b
Molecular Weight:148.2432
Molecular Formula:C8H20O2
InChIKey:GKMQWTVAAMITHR-KRSQWWHXSA-N
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Compound 10a
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-OCZOEHNFSA-N
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Compound 10b
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-OCZOEHNFSA-N
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Compound 10c
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-OCZOEHNFSA-N
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Compound 10d
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-OCZOEHNFSA-N
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Compound 11a
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-RUCXOUQFSA-N
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Compound 11b
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-RUCXOUQFSA-N
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Compound 11c
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-RUCXOUQFSA-N
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Compound 11d
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:JSFSXVIJPLTRKM-RUCXOUQFSA-N
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