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p-Synephrine enantiomers: binary phase diagram, crystal structure and kinetic stability of a metastable conglomerate monitored by nonlinear optics

hal.structure.identifierUnité de Technologies Chimiques et Biologiques pour la Santé [UTCBS - UM 4 (UMR 8258 / U1267)]
dc.contributor.authorIANNO, Veronica
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorCLEVERS, Simon
hal.structure.identifierSciences et Méthodes Séparatives [SMS]
dc.contributor.authorNEGRIER, Philippe
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorDUPRAY, Valerie
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorCOQUEREL, Gerard
hal.structure.identifierUnité de Technologies Chimiques et Biologiques pour la Santé [UTCBS - UM 4 (UMR 8258 / U1267)]
dc.contributor.authorESPEAU, Philippe
dc.date.issued2020
dc.description.abstractEnThe crystal structure of (S)-(+)-p-synephrine was refined at 296 K from X-ray powder diffraction. The compound crystallizes in the orthorhombic systemP2(1)2(1)2(1)with four molecules per unit cell and Z ' = 1. The cell parameters are equal toa= 6.5925(12) angstrom,b= 7.9915(14) angstrom, andc= 17.035(4) angstrom. The melting characteristics of the enantiomers were determined at high DSC scan rates. The pure enantiomers melt at T-fus= 176.6 +/- 0.9 degrees C with a melting enthalpy equal to 234.2 +/- 3.9 J g(-1). Coupling DSC and crystallographic analysis, a stable binary phase diagram between these chiral molecules was established taking into account the racemic compound. Two symmetrical eutectic invariants at: 172.7 +/- 0.5 degrees C for x = 0.05 and x = 0.95 were found pretty close to the melting temperature of the enantiomers. Additionally, the equimolar mechanical mixture of the two enantiomers led to a metastable conglomerate whose melting temperature was estimated to be 149 degrees C, thanks to the Schroder-van Laar relation. The activation energy of the transition from the metastable conglomerate toward the racemic compound was estimated to be E-a = 145 kJ mol(-1)by a nonlinear optical method. This new isothermal second harmonic generation application performed at different temperatures is of general applicability for the assessment of the activation energy associated with the irreversible heterogeneous reaction: <R> + <S> -> <RS>.
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.subject.enBEHAVIOR
dc.subject.enACID
dc.title.enp-Synephrine enantiomers: binary phase diagram, crystal structure and kinetic stability of a metastable conglomerate monitored by nonlinear optics
dc.typeArticle de revue
dc.identifier.doi10.1039/d0ce00841a
dc.subject.halPhysique [physics]/Physique [physics]/Chimie-Physique [physics.chem-ph]
dc.subject.halPhysique [physics]/Physique [physics]/Biophysique [physics.bio-ph]
bordeaux.journalCrystEngComm
bordeaux.page6071-6080
bordeaux.volume22
bordeaux.issue36
bordeaux.peerReviewedoui
hal.identifierhal-03290923
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-03290923v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=CrystEngComm&rft.date=2020&rft.volume=22&rft.issue=36&rft.spage=6071-6080&rft.epage=6071-6080&rft.au=IANNO,%20Veronica&CLEVERS,%20Simon&NEGRIER,%20Philippe&DUPRAY,%20Valerie&COQUEREL,%20Gerard&rft.genre=article


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