Chiroptical properties and racemization behavior of highly distorted donor-acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality

Hideaki Saito; Tadashi Mori; Yumi Origane; Takehiko Wada; Yoshihisa Inoue

doi:10.1002/chir.20427

Chiroptical properties and racemization behavior of highly distorted donor-acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality

Hideaki Saito, Tadashi Mori, Yumi Origane, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

Absolute configuration of optically active 7,12-bis(dicyanomethylene)-7,12- dihydrobenz[a]anthracene (1) with interconvertible planar chirality was determined by a comparison of experimental and theoretical circular dichroism (CD) spectra. Upon standing at ambient temperatures, 1 was found to spontaneously racemize, the rates of which were assessed through the separation profiles of chiral HPLC at 5-20°C and also from the CD spectral decay profiles at the same temperatures. Mechanism of the racemization was discussed.

Original language	English
Pages (from-to)	278-281
Number of pages	4
Journal	Chirality
Volume	20
Issue number	3-4
DOIs	https://doi.org/10.1002/chir.20427
Publication status	Published - 2008
Externally published	Yes

Keywords

Absolute configuration
Charge-transfer interaction
Circular dichroism
Planar chirality
Racemization
TD-DFT calculation
Tetracyanoquinodimethane

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

Access to Document

10.1002/chir.20427

Cite this

@article{7eaaa59c812141e09109f1a751c2a7b0,

title = "Chiroptical properties and racemization behavior of highly distorted donor-acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality",

abstract = "Absolute configuration of optically active 7,12-bis(dicyanomethylene)-7,12- dihydrobenz[a]anthracene (1) with interconvertible planar chirality was determined by a comparison of experimental and theoretical circular dichroism (CD) spectra. Upon standing at ambient temperatures, 1 was found to spontaneously racemize, the rates of which were assessed through the separation profiles of chiral HPLC at 5-20°C and also from the CD spectral decay profiles at the same temperatures. Mechanism of the racemization was discussed.",

keywords = "Absolute configuration, Charge-transfer interaction, Circular dichroism, Planar chirality, Racemization, TD-DFT calculation, Tetracyanoquinodimethane",

author = "Hideaki Saito and Tadashi Mori and Yumi Origane and Takehiko Wada and Yoshihisa Inoue",

year = "2008",

doi = "10.1002/chir.20427",

language = "English",

volume = "20",

pages = "278--281",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

number = "3-4",

}

TY - JOUR

T1 - Chiroptical properties and racemization behavior of highly distorted donor-acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality

AU - Saito, Hideaki

AU - Mori, Tadashi

AU - Origane, Yumi

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

PY - 2008

Y1 - 2008

N2 - Absolute configuration of optically active 7,12-bis(dicyanomethylene)-7,12- dihydrobenz[a]anthracene (1) with interconvertible planar chirality was determined by a comparison of experimental and theoretical circular dichroism (CD) spectra. Upon standing at ambient temperatures, 1 was found to spontaneously racemize, the rates of which were assessed through the separation profiles of chiral HPLC at 5-20°C and also from the CD spectral decay profiles at the same temperatures. Mechanism of the racemization was discussed.

AB - Absolute configuration of optically active 7,12-bis(dicyanomethylene)-7,12- dihydrobenz[a]anthracene (1) with interconvertible planar chirality was determined by a comparison of experimental and theoretical circular dichroism (CD) spectra. Upon standing at ambient temperatures, 1 was found to spontaneously racemize, the rates of which were assessed through the separation profiles of chiral HPLC at 5-20°C and also from the CD spectral decay profiles at the same temperatures. Mechanism of the racemization was discussed.

KW - Absolute configuration

KW - Charge-transfer interaction

KW - Circular dichroism

KW - Planar chirality

KW - Racemization

KW - TD-DFT calculation

KW - Tetracyanoquinodimethane

UR - http://www.scopus.com/inward/record.url?scp=39749183470&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=39749183470&partnerID=8YFLogxK

U2 - 10.1002/chir.20427

DO - 10.1002/chir.20427

M3 - Article

C2 - 17568437

AN - SCOPUS:39749183470

SN - 0899-0042

VL - 20

SP - 278

EP - 281

JO - Chirality

JF - Chirality

IS - 3-4

ER -

Chiroptical properties and racemization behavior of highly distorted donor-acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this