Poppy acid

Synthesis and crystal chemistry

Scott Lovell, Paramjeet Subramony, Bart Kahr

Research output: Contribution to journalArticle

Abstract

It had long ago been reported that poppy acid crystals encapsulate and orient a great variety of molecules during solution growth and in so doing seem to egregiously violate the principle of isomorphism. To comprehend this surprising host-guest chemistry, and exploit it for measuring anisotropic molecular properties, we attempted to carry out the oft-used literature synthesis of poppy acid, (3-hydroxy-2,6-dicarboxyγ-pyrone), but discovered that the standard procedures did not produce the title compound. We instead obtained a constitutional isomer as the potassium salt of 2-oxaloate-3- hydroxy-5-carboxyfuran. Therefore, we designed and carried out the first total synthesis of poppy acid. It crystallizes as either of two polymorphs, an orthorhombic form (Pbca) and a monoclinic form (C2/c), both characterized by weakly bonded layers consistent with perfect cleavages. The great majority of the dyes tested, 15 of 19, produced poppy acid crystals colored in particular growth sectors displaying strong linear dichroism. The observation of pronounced absorption anisotropy is consistent with a general mixed crystal growth mechanism in which the dyes substitute for poppy acid molecules within the layers and are further oriented in the direction of hydrogen bound rows of molecules within layers.

Original languageEnglish (US)
Pages (from-to)7020-7025
Number of pages6
JournalJournal of the American Chemical Society
Volume121
Issue number30
DOIs
StatePublished - Aug 4 1999

Fingerprint

Papaver
Crystal chemistry
Acids
Molecules
Coloring Agents
Dyes
Pyrones
Hydroxy Acids
Crystals
Anisotropy
Dichroism
Growth
Crystallization
Polymorphism
Crystal growth
Isomers
Potassium
Hydrogen
Salts
Observation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Poppy acid : Synthesis and crystal chemistry. / Lovell, Scott; Subramony, Paramjeet; Kahr, Bart.

In: Journal of the American Chemical Society, Vol. 121, No. 30, 04.08.1999, p. 7020-7025.

Research output: Contribution to journalArticle

Lovell, Scott ; Subramony, Paramjeet ; Kahr, Bart. / Poppy acid : Synthesis and crystal chemistry. In: Journal of the American Chemical Society. 1999 ; Vol. 121, No. 30. pp. 7020-7025.
@article{ef658bf96fe94671862fc27276b8e735,
title = "Poppy acid: Synthesis and crystal chemistry",
abstract = "It had long ago been reported that poppy acid crystals encapsulate and orient a great variety of molecules during solution growth and in so doing seem to egregiously violate the principle of isomorphism. To comprehend this surprising host-guest chemistry, and exploit it for measuring anisotropic molecular properties, we attempted to carry out the oft-used literature synthesis of poppy acid, (3-hydroxy-2,6-dicarboxyγ-pyrone), but discovered that the standard procedures did not produce the title compound. We instead obtained a constitutional isomer as the potassium salt of 2-oxaloate-3- hydroxy-5-carboxyfuran. Therefore, we designed and carried out the first total synthesis of poppy acid. It crystallizes as either of two polymorphs, an orthorhombic form (Pbca) and a monoclinic form (C2/c), both characterized by weakly bonded layers consistent with perfect cleavages. The great majority of the dyes tested, 15 of 19, produced poppy acid crystals colored in particular growth sectors displaying strong linear dichroism. The observation of pronounced absorption anisotropy is consistent with a general mixed crystal growth mechanism in which the dyes substitute for poppy acid molecules within the layers and are further oriented in the direction of hydrogen bound rows of molecules within layers.",
author = "Scott Lovell and Paramjeet Subramony and Bart Kahr",
year = "1999",
month = "8",
day = "4",
doi = "10.1021/ja990402a",
language = "English (US)",
volume = "121",
pages = "7020--7025",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "30",

}

TY - JOUR

T1 - Poppy acid

T2 - Synthesis and crystal chemistry

AU - Lovell, Scott

AU - Subramony, Paramjeet

AU - Kahr, Bart

PY - 1999/8/4

Y1 - 1999/8/4

N2 - It had long ago been reported that poppy acid crystals encapsulate and orient a great variety of molecules during solution growth and in so doing seem to egregiously violate the principle of isomorphism. To comprehend this surprising host-guest chemistry, and exploit it for measuring anisotropic molecular properties, we attempted to carry out the oft-used literature synthesis of poppy acid, (3-hydroxy-2,6-dicarboxyγ-pyrone), but discovered that the standard procedures did not produce the title compound. We instead obtained a constitutional isomer as the potassium salt of 2-oxaloate-3- hydroxy-5-carboxyfuran. Therefore, we designed and carried out the first total synthesis of poppy acid. It crystallizes as either of two polymorphs, an orthorhombic form (Pbca) and a monoclinic form (C2/c), both characterized by weakly bonded layers consistent with perfect cleavages. The great majority of the dyes tested, 15 of 19, produced poppy acid crystals colored in particular growth sectors displaying strong linear dichroism. The observation of pronounced absorption anisotropy is consistent with a general mixed crystal growth mechanism in which the dyes substitute for poppy acid molecules within the layers and are further oriented in the direction of hydrogen bound rows of molecules within layers.

AB - It had long ago been reported that poppy acid crystals encapsulate and orient a great variety of molecules during solution growth and in so doing seem to egregiously violate the principle of isomorphism. To comprehend this surprising host-guest chemistry, and exploit it for measuring anisotropic molecular properties, we attempted to carry out the oft-used literature synthesis of poppy acid, (3-hydroxy-2,6-dicarboxyγ-pyrone), but discovered that the standard procedures did not produce the title compound. We instead obtained a constitutional isomer as the potassium salt of 2-oxaloate-3- hydroxy-5-carboxyfuran. Therefore, we designed and carried out the first total synthesis of poppy acid. It crystallizes as either of two polymorphs, an orthorhombic form (Pbca) and a monoclinic form (C2/c), both characterized by weakly bonded layers consistent with perfect cleavages. The great majority of the dyes tested, 15 of 19, produced poppy acid crystals colored in particular growth sectors displaying strong linear dichroism. The observation of pronounced absorption anisotropy is consistent with a general mixed crystal growth mechanism in which the dyes substitute for poppy acid molecules within the layers and are further oriented in the direction of hydrogen bound rows of molecules within layers.

UR - http://www.scopus.com/inward/record.url?scp=0033523244&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033523244&partnerID=8YFLogxK

U2 - 10.1021/ja990402a

DO - 10.1021/ja990402a

M3 - Article

VL - 121

SP - 7020

EP - 7025

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 30

ER -