Supramolecular assembly in cinnamate structures: the influence of the ammonium ion and halogen interactions

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Supramolecular assembly in cinnamate structures: the influence of the ammonium ion and halogen interactions. / Chowdhury, M; Kariuki, Benson.

In: Crystal Growth and Design, Vol. 6, 01.03.2006, p. 774-780.

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@article{70722f80bae24b8b809c0704e10e7d49,
title = "Supramolecular assembly in cinnamate structures: the influence of the ammonium ion and halogen interactions",
abstract = "The role of the ammonium ion in directing self-assembly has been investigated, and the effect on the structure of changing halogen substituents has been examined. Ammonium 3-chloro- and 3-bromocinnamates, as well as ammonium 3-chlorocinnamate/3-chlorocinnamic acid and ammonium 3-bromocinnamate/3-bromocinnamic acid, have been synthesized and structurally characterized. The structures are layered with hydrophilic regions and double layers of anions. The ammonium ion tethers neighboring anions in a head-to-head relationship ca. 4 angstrom apart, the ideal distance for photoreaction. Changing the hydrogen bond donor-to-acceptor ratio from 2:1 to 5:4 does not change the general characteristics of the structures. Replacement of the meta ring substituent results in different structures. Apart from ammonium 3-chlorocinnamate/cinnamic acid, in which the double bonds are not parallel, the anion/acid units adopt the ideal geometry (distance and orientation) for photodimerization in all the other structures.",
author = "M Chowdhury and Benson Kariuki",
year = "2006",
month = mar,
day = "1",
doi = "10.1021/cg050604k",
language = "English",
volume = "6",
pages = "774--780",
journal = "Crystal Growth and Design",
issn = "1528-7483",
publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Supramolecular assembly in cinnamate structures: the influence of the ammonium ion and halogen interactions

AU - Chowdhury, M

AU - Kariuki, Benson

PY - 2006/3/1

Y1 - 2006/3/1

N2 - The role of the ammonium ion in directing self-assembly has been investigated, and the effect on the structure of changing halogen substituents has been examined. Ammonium 3-chloro- and 3-bromocinnamates, as well as ammonium 3-chlorocinnamate/3-chlorocinnamic acid and ammonium 3-bromocinnamate/3-bromocinnamic acid, have been synthesized and structurally characterized. The structures are layered with hydrophilic regions and double layers of anions. The ammonium ion tethers neighboring anions in a head-to-head relationship ca. 4 angstrom apart, the ideal distance for photoreaction. Changing the hydrogen bond donor-to-acceptor ratio from 2:1 to 5:4 does not change the general characteristics of the structures. Replacement of the meta ring substituent results in different structures. Apart from ammonium 3-chlorocinnamate/cinnamic acid, in which the double bonds are not parallel, the anion/acid units adopt the ideal geometry (distance and orientation) for photodimerization in all the other structures.

AB - The role of the ammonium ion in directing self-assembly has been investigated, and the effect on the structure of changing halogen substituents has been examined. Ammonium 3-chloro- and 3-bromocinnamates, as well as ammonium 3-chlorocinnamate/3-chlorocinnamic acid and ammonium 3-bromocinnamate/3-bromocinnamic acid, have been synthesized and structurally characterized. The structures are layered with hydrophilic regions and double layers of anions. The ammonium ion tethers neighboring anions in a head-to-head relationship ca. 4 angstrom apart, the ideal distance for photoreaction. Changing the hydrogen bond donor-to-acceptor ratio from 2:1 to 5:4 does not change the general characteristics of the structures. Replacement of the meta ring substituent results in different structures. Apart from ammonium 3-chlorocinnamate/cinnamic acid, in which the double bonds are not parallel, the anion/acid units adopt the ideal geometry (distance and orientation) for photodimerization in all the other structures.

UR - http://www.scopus.com/inward/record.url?scp=33645311525&partnerID=8YFLogxK

U2 - 10.1021/cg050604k

DO - 10.1021/cg050604k

M3 - Article

VL - 6

SP - 774

EP - 780

JO - Crystal Growth and Design

JF - Crystal Growth and Design

SN - 1528-7483

ER -