Planar hydrocarbons more optically active than their isomeric helicenes

Veronica L. Murphy, Bart Kahr

Research output: Contribution to journalArticle

Abstract

Comparisons are made of the calculated optical rotation tensors of C 2v-symmetric, polyaromatic hydrocarbons and their [5]helicene, [6]helicene, and [7]helicene isomers. Seven -shaped, planar compounds had, in each case, larger computed tensor elements than the chiral helicenes. Merely obviating the condition of solution averaging wholly changes expectations of the magnitudes and etiologies of optical activity. Symmetries of achiral compounds facilitate semiquantitative correlations between structure and optical rotation.

Original languageEnglish (US)
Pages (from-to)12918-12921
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number33
DOIs
StatePublished - Aug 24 2011

Fingerprint

Optical rotation
Optical Rotation
Hydrocarbons
Tensors
Isomers
helicenes

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Planar hydrocarbons more optically active than their isomeric helicenes. / Murphy, Veronica L.; Kahr, Bart.

In: Journal of the American Chemical Society, Vol. 133, No. 33, 24.08.2011, p. 12918-12921.

Research output: Contribution to journalArticle

@article{a94ff3deb066405fbb23416e23707261,
title = "Planar hydrocarbons more optically active than their isomeric helicenes",
abstract = "Comparisons are made of the calculated optical rotation tensors of C 2v-symmetric, polyaromatic hydrocarbons and their [5]helicene, [6]helicene, and [7]helicene isomers. Seven -shaped, planar compounds had, in each case, larger computed tensor elements than the chiral helicenes. Merely obviating the condition of solution averaging wholly changes expectations of the magnitudes and etiologies of optical activity. Symmetries of achiral compounds facilitate semiquantitative correlations between structure and optical rotation.",
author = "Murphy, {Veronica L.} and Bart Kahr",
year = "2011",
month = "8",
day = "24",
doi = "10.1021/ja203509s",
language = "English (US)",
volume = "133",
pages = "12918--12921",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "33",

}

TY - JOUR

T1 - Planar hydrocarbons more optically active than their isomeric helicenes

AU - Murphy, Veronica L.

AU - Kahr, Bart

PY - 2011/8/24

Y1 - 2011/8/24

N2 - Comparisons are made of the calculated optical rotation tensors of C 2v-symmetric, polyaromatic hydrocarbons and their [5]helicene, [6]helicene, and [7]helicene isomers. Seven -shaped, planar compounds had, in each case, larger computed tensor elements than the chiral helicenes. Merely obviating the condition of solution averaging wholly changes expectations of the magnitudes and etiologies of optical activity. Symmetries of achiral compounds facilitate semiquantitative correlations between structure and optical rotation.

AB - Comparisons are made of the calculated optical rotation tensors of C 2v-symmetric, polyaromatic hydrocarbons and their [5]helicene, [6]helicene, and [7]helicene isomers. Seven -shaped, planar compounds had, in each case, larger computed tensor elements than the chiral helicenes. Merely obviating the condition of solution averaging wholly changes expectations of the magnitudes and etiologies of optical activity. Symmetries of achiral compounds facilitate semiquantitative correlations between structure and optical rotation.

UR - http://www.scopus.com/inward/record.url?scp=80051762043&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80051762043&partnerID=8YFLogxK

U2 - 10.1021/ja203509s

DO - 10.1021/ja203509s

M3 - Article

C2 - 21793486

AN - SCOPUS:80051762043

VL - 133

SP - 12918

EP - 12921

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 33

ER -