Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra

Takahiro Furo; Tadashi Mori; Yumi Origane; Takehiko Wada; Hiroshi Izumi; Yoshihisa Inoue

doi:10.1002/chir.20233

Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra

Takahiro Furo, Tadashi Mori, Yumi Origane, Takehiko Wada, Hiroshi Izumi, Yoshihisa Inoue

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

16 Citations (Scopus)

Abstract

Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7-bis(methoxycarbonyl)-12,15-dimethoxy-[2.2]paracyclophanes (1 and 2), and density functional theory CDFT) calculations were performed at the B3LYP/6-31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)-enantiomers as (4S_P;12S_P)-1 and (4S_p;12R_p)-2, respectively.

Original language	English
Pages (from-to)	205-211
Number of pages	7
Journal	Chirality
Volume	18
Issue number	3
DOIs	https://doi.org/10.1002/chir.20233
Publication status	Published - 2006 Mar 10
Externally published	Yes

Keywords

Charge-transfer interaction
Chiral cyclophane
DFT calculation
Exciton coupling method
Vibrational circular dichroism spectroscopy

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.20233

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title = "Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra",

abstract = "Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7-bis(methoxycarbonyl)-12,15-dimethoxy-[2.2]paracyclophanes (1 and 2), and density functional theory CDFT) calculations were performed at the B3LYP/6-31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)-enantiomers as (4SP;12SP)-1 and (4Sp;12Rp)-2, respectively.",

keywords = "Charge-transfer interaction, Chiral cyclophane, DFT calculation, Exciton coupling method, Vibrational circular dichroism spectroscopy",

author = "Takahiro Furo and Tadashi Mori and Yumi Origane and Takehiko Wada and Hiroshi Izumi and Yoshihisa Inoue",

year = "2006",

month = mar,

day = "10",

doi = "10.1002/chir.20233",

language = "English",

volume = "18",

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journal = "Chirality",

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TY - JOUR

T1 - Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra

AU - Furo, Takahiro

AU - Mori, Tadashi

AU - Origane, Yumi

AU - Wada, Takehiko

AU - Izumi, Hiroshi

AU - Inoue, Yoshihisa

PY - 2006/3/10

Y1 - 2006/3/10

N2 - Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7-bis(methoxycarbonyl)-12,15-dimethoxy-[2.2]paracyclophanes (1 and 2), and density functional theory CDFT) calculations were performed at the B3LYP/6-31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)-enantiomers as (4SP;12SP)-1 and (4Sp;12Rp)-2, respectively.

AB - Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7-bis(methoxycarbonyl)-12,15-dimethoxy-[2.2]paracyclophanes (1 and 2), and density functional theory CDFT) calculations were performed at the B3LYP/6-31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)-enantiomers as (4SP;12SP)-1 and (4Sp;12Rp)-2, respectively.

KW - Charge-transfer interaction

KW - Chiral cyclophane

KW - DFT calculation

KW - Exciton coupling method

KW - Vibrational circular dichroism spectroscopy

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Absolute configuration determination of donor-acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra

Abstract

Keywords

ASJC Scopus subject areas

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