The crystal packing of a strongly dipolar piperazinedione

B. Jagadish; Lawrence J. Williams; Michael D. Carducci; Christian Bosshard; Eugene A. Mash

doi:10.1016/S0040-4039(00)01623-3

The crystal packing of a strongly dipolar piperazinedione

B. Jagadish, Lawrence J. Williams, Michael D. Carducci, Christian Bosshard, Eugene A. Mash

Chemistry and Biochemistry

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

11 Scopus citations

Abstract

A strongly dipolar piperazine-2,5-dione was synthesized in enantiomerically pure form, crystallized from DMSO, and the supramolecular organization of the crystals determined by X-ray crystallography. In contrast with non-polar or weakly polar piperazinediones of similar molecular topography, which form tapes by reciprocal intermolecular amide-to-amide hydrogen bonding, the strongly dipolar piperazinedione participated in hydrogen bonding with occluded DMSO. The dipoles of the piperazinedione molecules were aligned and were opposed by the dipoles of the DMSO molecules. The cocrystals exhibited second harmonic generation when subjected to pulsed irradiation.

Original language	English (US)
Pages (from-to)	9483-9487
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(00)01623-3
State	Published - Dec 2 2000

Keywords

Crystallization
Optical properties
Piperazinediones
Supramolecular chemistry
X-ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)01623-3

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title = "The crystal packing of a strongly dipolar piperazinedione",

abstract = "A strongly dipolar piperazine-2,5-dione was synthesized in enantiomerically pure form, crystallized from DMSO, and the supramolecular organization of the crystals determined by X-ray crystallography. In contrast with non-polar or weakly polar piperazinediones of similar molecular topography, which form tapes by reciprocal intermolecular amide-to-amide hydrogen bonding, the strongly dipolar piperazinedione participated in hydrogen bonding with occluded DMSO. The dipoles of the piperazinedione molecules were aligned and were opposed by the dipoles of the DMSO molecules. The cocrystals exhibited second harmonic generation when subjected to pulsed irradiation.",

keywords = "Crystallization, Optical properties, Piperazinediones, Supramolecular chemistry, X-ray crystal structures",

author = "B. Jagadish and Williams, {Lawrence J.} and Carducci, {Michael D.} and Christian Bosshard and Mash, {Eugene A.}",

note = "Funding Information: Financial support of this research from the ONR through the Center for Advanced Multifunctional Nonlinear Optical Polymers and Molecular Assemblies, from Research Corporation, and from the University of Arizona through the Materials Characterization Program and the Office of the Vice President for Research is gratefully acknowledged.",

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doi = "10.1016/S0040-4039(00)01623-3",

language = "English (US)",

volume = "41",

pages = "9483--9487",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - The crystal packing of a strongly dipolar piperazinedione

AU - Jagadish, B.

AU - Williams, Lawrence J.

AU - Carducci, Michael D.

AU - Bosshard, Christian

AU - Mash, Eugene A.

N1 - Funding Information: Financial support of this research from the ONR through the Center for Advanced Multifunctional Nonlinear Optical Polymers and Molecular Assemblies, from Research Corporation, and from the University of Arizona through the Materials Characterization Program and the Office of the Vice President for Research is gratefully acknowledged.

PY - 2000/12/2

Y1 - 2000/12/2

N2 - A strongly dipolar piperazine-2,5-dione was synthesized in enantiomerically pure form, crystallized from DMSO, and the supramolecular organization of the crystals determined by X-ray crystallography. In contrast with non-polar or weakly polar piperazinediones of similar molecular topography, which form tapes by reciprocal intermolecular amide-to-amide hydrogen bonding, the strongly dipolar piperazinedione participated in hydrogen bonding with occluded DMSO. The dipoles of the piperazinedione molecules were aligned and were opposed by the dipoles of the DMSO molecules. The cocrystals exhibited second harmonic generation when subjected to pulsed irradiation.

AB - A strongly dipolar piperazine-2,5-dione was synthesized in enantiomerically pure form, crystallized from DMSO, and the supramolecular organization of the crystals determined by X-ray crystallography. In contrast with non-polar or weakly polar piperazinediones of similar molecular topography, which form tapes by reciprocal intermolecular amide-to-amide hydrogen bonding, the strongly dipolar piperazinedione participated in hydrogen bonding with occluded DMSO. The dipoles of the piperazinedione molecules were aligned and were opposed by the dipoles of the DMSO molecules. The cocrystals exhibited second harmonic generation when subjected to pulsed irradiation.

KW - Crystallization

KW - Optical properties

KW - Piperazinediones

KW - Supramolecular chemistry

KW - X-ray crystal structures

UR - http://www.scopus.com/inward/record.url?scp=0034598018&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034598018&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)01623-3

DO - 10.1016/S0040-4039(00)01623-3

M3 - Article

AN - SCOPUS:0034598018

VL - 41

SP - 9483

EP - 9487

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 49

ER -

The crystal packing of a strongly dipolar piperazinedione

Abstract

Keywords

ASJC Scopus subject areas

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