(E)-o-stilbenecarboxylic acid and its p-methyl, chloro and methoxy derivatives

Hiroshi Hamazaki; Shigeru Ohba; Fumio Toda; Hideaki Takumi

doi:10.1107/S0108270196015673

(E)-o-stilbenecarboxylic acid and its p-methyl, chloro and methoxy derivatives

Hiroshi Hamazaki, Shigeru Ohba, Fumio Toda, Hideaki Takumi

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

7 Citations (Scopus)

Abstract

The crystal structures of the title compounds, (E)-stilbene-1-carboxylic acid, C₁₅H₁₂O₂, (Ia), (E)-4′-methylstilbene-1-carboxylic acid, C₁₆H₁₄O₂, (Ib), (E)-4′-chlorostilbene-1-carboxylic acid, C₁₅H₁₁ClO₂, (Ic) and (Ic′), and (E)-4′-methoxystilbene-1-carboxylic acid, C₁₆H₁₄O₃, (Id), have been determined. The chloro derivative shows polymorphism, with prisms, (Ic), being obtained from ether/hexane solution and needle crystals, (Ic′), being obtained from ethanol solution. The latter is isostructural with (Id). The selectivities of the products to the addition reaction of bromine are different, however, suggesting that the bromonium ion intermediate is stabilized by a resonance contribution of the p-MeO group.

Original language	English
Pages (from-to)	620-624
Number of pages	5
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	53
Issue number	5
DOIs	https://doi.org/10.1107/S0108270196015673
Publication status	Published - 1997 May 15
Externally published	Yes

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)

Access to Document

10.1107/S0108270196015673

Cite this

@article{a6c070049d0d47ad9d284ee13e11e6af,

title = "(E)-o-stilbenecarboxylic acid and its p-methyl, chloro and methoxy derivatives",

abstract = "The crystal structures of the title compounds, (E)-stilbene-1-carboxylic acid, C15H12O2, (Ia), (E)-4′-methylstilbene-1-carboxylic acid, C16H14O2, (Ib), (E)-4′-chlorostilbene-1-carboxylic acid, C15H11ClO2, (Ic) and (Ic′), and (E)-4′-methoxystilbene-1-carboxylic acid, C16H14O3, (Id), have been determined. The chloro derivative shows polymorphism, with prisms, (Ic), being obtained from ether/hexane solution and needle crystals, (Ic′), being obtained from ethanol solution. The latter is isostructural with (Id). The selectivities of the products to the addition reaction of bromine are different, however, suggesting that the bromonium ion intermediate is stabilized by a resonance contribution of the p-MeO group.",

author = "Hiroshi Hamazaki and Shigeru Ohba and Fumio Toda and Hideaki Takumi",

year = "1997",

month = may,

day = "15",

doi = "10.1107/S0108270196015673",

language = "English",

volume = "53",

pages = "620--624",

journal = "Acta Crystallographica Section C: Crystal Structure Communications",

issn = "0108-2701",

publisher = "International Union of Crystallography",

number = "5",

}

TY - JOUR

T1 - (E)-o-stilbenecarboxylic acid and its p-methyl, chloro and methoxy derivatives

AU - Hamazaki, Hiroshi

AU - Ohba, Shigeru

AU - Toda, Fumio

AU - Takumi, Hideaki

PY - 1997/5/15

Y1 - 1997/5/15

N2 - The crystal structures of the title compounds, (E)-stilbene-1-carboxylic acid, C15H12O2, (Ia), (E)-4′-methylstilbene-1-carboxylic acid, C16H14O2, (Ib), (E)-4′-chlorostilbene-1-carboxylic acid, C15H11ClO2, (Ic) and (Ic′), and (E)-4′-methoxystilbene-1-carboxylic acid, C16H14O3, (Id), have been determined. The chloro derivative shows polymorphism, with prisms, (Ic), being obtained from ether/hexane solution and needle crystals, (Ic′), being obtained from ethanol solution. The latter is isostructural with (Id). The selectivities of the products to the addition reaction of bromine are different, however, suggesting that the bromonium ion intermediate is stabilized by a resonance contribution of the p-MeO group.

AB - The crystal structures of the title compounds, (E)-stilbene-1-carboxylic acid, C15H12O2, (Ia), (E)-4′-methylstilbene-1-carboxylic acid, C16H14O2, (Ib), (E)-4′-chlorostilbene-1-carboxylic acid, C15H11ClO2, (Ic) and (Ic′), and (E)-4′-methoxystilbene-1-carboxylic acid, C16H14O3, (Id), have been determined. The chloro derivative shows polymorphism, with prisms, (Ic), being obtained from ether/hexane solution and needle crystals, (Ic′), being obtained from ethanol solution. The latter is isostructural with (Id). The selectivities of the products to the addition reaction of bromine are different, however, suggesting that the bromonium ion intermediate is stabilized by a resonance contribution of the p-MeO group.

UR - http://www.scopus.com/inward/record.url?scp=3242850856&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=3242850856&partnerID=8YFLogxK

U2 - 10.1107/S0108270196015673

DO - 10.1107/S0108270196015673

M3 - Article

AN - SCOPUS:3242850856

SN - 0108-2701

VL - 53

SP - 620

EP - 624

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

IS - 5

ER -

(E)-o-stilbenecarboxylic acid and its p-methyl, chloro and methoxy derivatives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this