Exploring the Crystal Landscape of Mandelamide and Chiral Resolution via Cocrystallization

Shan Huang; Deirbhile Fitzgerald; Samuel A. Koledoye; Stuart G. Collins; Anita R. Maguire; Simon E. Lawrence

doi:10.1021/acs.cgd.3c01513

Exploring the Crystal Landscape of Mandelamide and Chiral Resolution via Cocrystallization

Shan Huang
, Deirbhile Fitzgerald
, Samuel A. Koledoye
, Stuart G. Collins
, Anita R. Maguire
, Simon E. Lawrence

University College Cork

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

Abstract

The crystal structures of (±)-mandelamide, S-mandelamide, and enantioenriched mandelamide (94 S : 6 R) were determined. Diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline were synthesized. The diastereomeric cocrystal pairs of S-mandelamide with S/R-mandelic acid form 1:1 cocrystals in each case, while the diastereomeric cocrystal pairs of S-mandelamide with proline have different stoichiometries. Preliminary investigation of this diastereomeric cocrystal system for chiral resolution shows promise.

Original language	English
Pages (from-to)	1-12
Number of pages	12
Journal	Crystal Growth and Design
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/acs.cgd.3c01513
Publication status	Published - 1 Jan 2025

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10.1021/acs.cgd.3c01513

https://hdl.handle.net/10468/16778Licence: CC BY

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title = "Exploring the Crystal Landscape of Mandelamide and Chiral Resolution via Cocrystallization",

abstract = "The crystal structures of (±)-mandelamide, S-mandelamide, and enantioenriched mandelamide (94 S : 6 R) were determined. Diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline were synthesized. The diastereomeric cocrystal pairs of S-mandelamide with S/R-mandelic acid form 1:1 cocrystals in each case, while the diastereomeric cocrystal pairs of S-mandelamide with proline have different stoichiometries. Preliminary investigation of this diastereomeric cocrystal system for chiral resolution shows promise.",

author = "Shan Huang and Deirbhile Fitzgerald and Koledoye, \{Samuel A.\} and Collins, \{Stuart G.\} and Maguire, \{Anita R.\} and Lawrence, \{Simon E.\}",

note = "Publisher Copyright: {\textcopyright} 2024 The Authors. Published by American Chemical Society.",

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AU - Huang, Shan

AU - Fitzgerald, Deirbhile

AU - Koledoye, Samuel A.

AU - Collins, Stuart G.

AU - Maguire, Anita R.

AU - Lawrence, Simon E.

PY - 2025/1/1

Y1 - 2025/1/1

N2 - The crystal structures of (±)-mandelamide, S-mandelamide, and enantioenriched mandelamide (94 S : 6 R) were determined. Diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline were synthesized. The diastereomeric cocrystal pairs of S-mandelamide with S/R-mandelic acid form 1:1 cocrystals in each case, while the diastereomeric cocrystal pairs of S-mandelamide with proline have different stoichiometries. Preliminary investigation of this diastereomeric cocrystal system for chiral resolution shows promise.

AB - The crystal structures of (±)-mandelamide, S-mandelamide, and enantioenriched mandelamide (94 S : 6 R) were determined. Diastereomeric cocrystal pairs of S-mandelamide with both enantiomers of mandelic acid and proline were synthesized. The diastereomeric cocrystal pairs of S-mandelamide with S/R-mandelic acid form 1:1 cocrystals in each case, while the diastereomeric cocrystal pairs of S-mandelamide with proline have different stoichiometries. Preliminary investigation of this diastereomeric cocrystal system for chiral resolution shows promise.

UR - https://www.scopus.com/pages/publications/85217956869

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DO - 10.1021/acs.cgd.3c01513

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SN - 1528-7483

VL - 25

SP - 1

EP - 12

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 1

ER -

Exploring the Crystal Landscape of Mandelamide and Chiral Resolution via Cocrystallization

Abstract

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