Chiroptical structure-property relations in cyclo[18]carbon and its in silico hydrogenation products

Veronica L. Murphy, Camille Farfan, Bart Kahr

Research output: Contribution to journalArticle

Abstract

The anisotropy of the optical activity of cyclo[18]carbon (C18), fully hydrogenated C18 (C18H36), and 26 hydrogenated compounds of intermediate composition, C18H2n, n = 1,2..17, were computed. These compounds were selected because they resemble loops of wire. The maximum gyration for acetylenic and cumulenic subgroups of compounds was linearly proportional to the product of the geometric area over which the charge can circulate, multiplied by the largest separation between carbon atoms on opposing sides of the loops. These geometric quantities can be likened to transition magnetic dipole moments and transition electric dipole moments, respectively, that can be generated in electronic excitations and which contribute in the main to nonresonant optical activity. The correlation between a computed geometric product of distance and area, and a quantum chemical property, establishes that chiroptical structure-activity relationships can be well established for judiciously chosen series of comparatively large compounds.

Original languageEnglish (US)
JournalChirality
DOIs
StateAccepted/In press - Jan 1 2018

Fingerprint

Optical Rotation
Hydrogenation
Computer Simulation
Carbon
Electric dipole moments
Anisotropy
Structure-Activity Relationship
Magnetic moments
Chemical properties
Wire
Atoms
Chemical analysis
3-(5-nitrofuryl)-7-(5-nitrofurfurylidene)-3,3a,4,5,6,7-hexahydro-2H-indazole

Keywords

  • Aromaticity
  • Cyclo[18]carbon
  • Gyration
  • Optical activity
  • Optical rotation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Chiroptical structure-property relations in cyclo[18]carbon and its in silico hydrogenation products. / Murphy, Veronica L.; Farfan, Camille; Kahr, Bart.

In: Chirality, 01.01.2018.

Research output: Contribution to journalArticle

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