Optical rotation of achiral compounds

Kacey Claborn, Christine Isborn, Werner Kaminsky, Bart Kahr

Research output: Contribution to journalArticle

Abstract

Oriented achiral molecules and crystals with D2d symmetry or one of its non-enantiomorphous subgroups, S4, C2v, or C s, can rotate the plane of transmitted polarized light incident in a general direction. This well-established fact of crystal optics is contrary to the teaching of optical activity to students of organic chemistry. This Minireview gives an overview of the measurement and calculation of the chiroptical properties of some achiral compounds and crystals. Methane derivatives with four identical ligands related by reflection symmetry are quintessential optically inactive compounds according to the logic of van 't Hoff. Analysis of the optical activity of simple achiral compounds such as H2O and NH3 provides general aspects of chiroptics that are not readily broached when considering chiral compounds exclusively. We show here, through the use of group theoretical arguments, the transformation properties of tensors, and diagrams, why some achiral, acentric compounds are optically active while others are not.

Original languageEnglish (US)
Pages (from-to)5706-5717
Number of pages12
JournalAngewandte Chemie - International Edition
Volume47
Issue number31
DOIs
StatePublished - Jul 21 2008

Fingerprint

Optical rotation
Crystals
Methane
Crystal symmetry
Light polarization
Tensors
Optics
Teaching
Ligands
Students
Derivatives
Molecules

Keywords

  • Circular dichroism
  • Crystallography
  • Molecular chirality
  • Optical activity
  • Polarimetry

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Optical rotation of achiral compounds. / Claborn, Kacey; Isborn, Christine; Kaminsky, Werner; Kahr, Bart.

In: Angewandte Chemie - International Edition, Vol. 47, No. 31, 21.07.2008, p. 5706-5717.

Research output: Contribution to journalArticle

Claborn, Kacey ; Isborn, Christine ; Kaminsky, Werner ; Kahr, Bart. / Optical rotation of achiral compounds. In: Angewandte Chemie - International Edition. 2008 ; Vol. 47, No. 31. pp. 5706-5717.
@article{455210a9cc0b4ef4b421b557af131cc3,
title = "Optical rotation of achiral compounds",
abstract = "Oriented achiral molecules and crystals with D2d symmetry or one of its non-enantiomorphous subgroups, S4, C2v, or C s, can rotate the plane of transmitted polarized light incident in a general direction. This well-established fact of crystal optics is contrary to the teaching of optical activity to students of organic chemistry. This Minireview gives an overview of the measurement and calculation of the chiroptical properties of some achiral compounds and crystals. Methane derivatives with four identical ligands related by reflection symmetry are quintessential optically inactive compounds according to the logic of van 't Hoff. Analysis of the optical activity of simple achiral compounds such as H2O and NH3 provides general aspects of chiroptics that are not readily broached when considering chiral compounds exclusively. We show here, through the use of group theoretical arguments, the transformation properties of tensors, and diagrams, why some achiral, acentric compounds are optically active while others are not.",
keywords = "Circular dichroism, Crystallography, Molecular chirality, Optical activity, Polarimetry",
author = "Kacey Claborn and Christine Isborn and Werner Kaminsky and Bart Kahr",
year = "2008",
month = "7",
day = "21",
doi = "10.1002/anie.200704559",
language = "English (US)",
volume = "47",
pages = "5706--5717",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "31",

}

TY - JOUR

T1 - Optical rotation of achiral compounds

AU - Claborn, Kacey

AU - Isborn, Christine

AU - Kaminsky, Werner

AU - Kahr, Bart

PY - 2008/7/21

Y1 - 2008/7/21

N2 - Oriented achiral molecules and crystals with D2d symmetry or one of its non-enantiomorphous subgroups, S4, C2v, or C s, can rotate the plane of transmitted polarized light incident in a general direction. This well-established fact of crystal optics is contrary to the teaching of optical activity to students of organic chemistry. This Minireview gives an overview of the measurement and calculation of the chiroptical properties of some achiral compounds and crystals. Methane derivatives with four identical ligands related by reflection symmetry are quintessential optically inactive compounds according to the logic of van 't Hoff. Analysis of the optical activity of simple achiral compounds such as H2O and NH3 provides general aspects of chiroptics that are not readily broached when considering chiral compounds exclusively. We show here, through the use of group theoretical arguments, the transformation properties of tensors, and diagrams, why some achiral, acentric compounds are optically active while others are not.

AB - Oriented achiral molecules and crystals with D2d symmetry or one of its non-enantiomorphous subgroups, S4, C2v, or C s, can rotate the plane of transmitted polarized light incident in a general direction. This well-established fact of crystal optics is contrary to the teaching of optical activity to students of organic chemistry. This Minireview gives an overview of the measurement and calculation of the chiroptical properties of some achiral compounds and crystals. Methane derivatives with four identical ligands related by reflection symmetry are quintessential optically inactive compounds according to the logic of van 't Hoff. Analysis of the optical activity of simple achiral compounds such as H2O and NH3 provides general aspects of chiroptics that are not readily broached when considering chiral compounds exclusively. We show here, through the use of group theoretical arguments, the transformation properties of tensors, and diagrams, why some achiral, acentric compounds are optically active while others are not.

KW - Circular dichroism

KW - Crystallography

KW - Molecular chirality

KW - Optical activity

KW - Polarimetry

UR - http://www.scopus.com/inward/record.url?scp=53649099524&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=53649099524&partnerID=8YFLogxK

U2 - 10.1002/anie.200704559

DO - 10.1002/anie.200704559

M3 - Article

C2 - 18600811

AN - SCOPUS:53649099524

VL - 47

SP - 5706

EP - 5717

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 31

ER -