Structural aspects of optical resolutions. Optical resolution of (R,S)-mandelic acid. DSC and X-ray studies of the diastereoisomeric salts

Mária Acs, Elisabeth Novotny-Bregger, Kálmán Simon, G. Argay

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Abstract

The diastereoisomeric salt pair formed during the resolution of mandelic acid (MA) using (R)-2-tert-butyl-3-methylimidazolidin-4-one (BMI) has been studied by DSC and X-ray crystallographic methods. Both diastereoisomers crystallize in a monoclinic system with space group P21; unit cell parameters for the less soluble R-R isomer: a = 11.484(1), b = 6.027(1), c = 11.951(1) Å, β = 98.77(1)°, V = 817.5(3) Å3; for the more soluble R-S diastereoisomer a = 11.170(1), b = 5.975(1), c = 13.327(1) Å, β = 111.95(1)°, V = 825.0(3) Å3. The structures were solved by direct methods and refined to a final R value of 0.044 and 0.057, respectively.

Original languageEnglish
Pages (from-to)2011-2017
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number11
Publication statusPublished - 1992

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Isomers
Salts
X rays
mandelic acid

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  • Chemistry(all)

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Structural aspects of optical resolutions. Optical resolution of (R,S)-mandelic acid. DSC and X-ray studies of the diastereoisomeric salts. / Acs, Mária; Novotny-Bregger, Elisabeth; Simon, Kálmán; Argay, G.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 11, 1992, p. 2011-2017.

Research output: Contribution to journalArticle

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abstract = "The diastereoisomeric salt pair formed during the resolution of mandelic acid (MA) using (R)-2-tert-butyl-3-methylimidazolidin-4-one (BMI) has been studied by DSC and X-ray crystallographic methods. Both diastereoisomers crystallize in a monoclinic system with space group P21; unit cell parameters for the less soluble R-R isomer: a = 11.484(1), b = 6.027(1), c = 11.951(1) {\AA}, β = 98.77(1)°, V = 817.5(3) {\AA}3; for the more soluble R-S diastereoisomer a = 11.170(1), b = 5.975(1), c = 13.327(1) {\AA}, β = 111.95(1)°, V = 825.0(3) {\AA}3. The structures were solved by direct methods and refined to a final R value of 0.044 and 0.057, respectively.",
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AU - Novotny-Bregger, Elisabeth

AU - Simon, Kálmán

AU - Argay, G.

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N2 - The diastereoisomeric salt pair formed during the resolution of mandelic acid (MA) using (R)-2-tert-butyl-3-methylimidazolidin-4-one (BMI) has been studied by DSC and X-ray crystallographic methods. Both diastereoisomers crystallize in a monoclinic system with space group P21; unit cell parameters for the less soluble R-R isomer: a = 11.484(1), b = 6.027(1), c = 11.951(1) Å, β = 98.77(1)°, V = 817.5(3) Å3; for the more soluble R-S diastereoisomer a = 11.170(1), b = 5.975(1), c = 13.327(1) Å, β = 111.95(1)°, V = 825.0(3) Å3. The structures were solved by direct methods and refined to a final R value of 0.044 and 0.057, respectively.

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