Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal

Natalia Tumanova; Ricky Payen; Géraldine Springuel; Bernadette Norberg; Koen Robeyns; Cécile Le Duff; Johan Wouters; Tom Leyssens

doi:10.1016/j.molstruc.2016.07.109

Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal

Natalia Tumanova, Ricky Payen, Géraldine Springuel, Bernadette Norberg, Koen Robeyns, Cécile Le Duff, Johan Wouters, Tom Leyssens

Unite de recherche en chimie physique, theorique et structurale

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.

langue originale	Anglais
Pages (de - à)	397-402
Nombre de pages	6
journal	Journal of molecular structure
Volume	1127
Les DOIs	https://doi.org/10.1016/j.molstruc.2016.07.109
Etat de la publication	Publié - 5 janv. 2017

Accès au document

10.1016/j.molstruc.2016.07.109

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CCDC 1400250: Experimental Crystal Structure Determination
Le Duff, C. (Contributeur), Leyssens, T. (Contributeur), NORBERG, B. (Contributeur), Payen, R. (Contributeur), Robeyns, K. (Contributeur), Springuel, G. (Contributeur), Tumanova, N. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2016
DOI: 10.5517/ccdc.csd.cc1j02cz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1j02cz&sid=DataCite
Ensemble de données
CCDC 1060627: Experimental Crystal Structure Determination
Le Duff, C. (Contributeur), Leyssens, T. (Contributeur), NORBERG, B. (Contributeur), Payen, R. (Contributeur), Robeyns, K. (Contributeur), Springuel, G. (Contributeur), Tumanova, N. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2016
DOI: 10.5517/ccdc.csd.cc14lns5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc14lns5&sid=DataCite
Ensemble de données

Contient cette citation

@article{b0eec9255cf140fb92280f4fef37842b,

title = "Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal",

abstract = "This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.",

keywords = "Cocrystallization, Esterification, Mandelic acid",

author = "Natalia Tumanova and Ricky Payen and G{\'e}raldine Springuel and Bernadette Norberg and Koen Robeyns and {Le Duff}, C{\'e}cile and Johan Wouters and Tom Leyssens",

note = "Funding Information: The authors thank the UCL , Unamur and FNRS ( PDR T009913F , T016913 , FRIA grant) for financial support. Publisher Copyright: {\textcopyright} 2016 Elsevier B.V. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

year = "2017",

month = jan,

day = "5",

doi = "10.1016/j.molstruc.2016.07.109",

language = "English",

volume = "1127",

pages = "397--402",

journal = "Journal of molecular structure",

issn = "0022-2860",

publisher = "Elsevier",

}

TY - JOUR

T1 - Cocrystallization out of the blue

T2 - DL-mandelic acid/ethyl-DL-mandelate cocrystal

AU - Tumanova, Natalia

AU - Payen, Ricky

AU - Springuel, Géraldine

AU - Norberg, Bernadette

AU - Robeyns, Koen

AU - Le Duff, Cécile

AU - Wouters, Johan

AU - Leyssens, Tom

N1 - Funding Information: The authors thank the UCL , Unamur and FNRS ( PDR T009913F , T016913 , FRIA grant) for financial support. Publisher Copyright: © 2016 Elsevier B.V. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2017/1/5

Y1 - 2017/1/5

N2 - This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.

AB - This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.

KW - Cocrystallization

KW - Esterification

KW - Mandelic acid

UR - http://www.scopus.com/inward/record.url?scp=84982797777&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2016.07.109

DO - 10.1016/j.molstruc.2016.07.109

M3 - Article

AN - SCOPUS:84982797777

SN - 0022-2860

VL - 1127

SP - 397

EP - 402

JO - Journal of molecular structure

JF - Journal of molecular structure

ER -

Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Plateforme Technologique Calcul Intensif

Ensembles de données

CCDC 1400250: Experimental Crystal Structure Determination

CCDC 1060627: Experimental Crystal Structure Determination

Contient cette citation