Directing the Viedma ripening of ethylenediammonium sulfate using ": Tailor-made " chiral additives

Thi Phuong Thao Nguyen; Pui Shan Monica Cheung; Liora Werber; Jacinthe Gagnon; Reajean Sivakumar; Cameron Lennox; Aaron Sossin; Yitzhak Mastai; Louis A. Cuccia

doi:https://doi.org/10.1039/c6cc06534a

Directing the Viedma ripening of ethylenediammonium sulfate using ": Tailor-made " chiral additives

Thi Phuong Thao Nguyen, Pui Shan Monica Cheung, Liora Werber, Jacinthe Gagnon, Reajean Sivakumar, Cameron Lennox, Aaron Sossin, Yitzhak Mastai, Louis A. Cuccia

Department of Chemistry

Bar-Ilan University

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

Abstract

Both enantiomers of trans-cyclohexane-1,2-diammonium sulfate and trans-1,2-diphenylethylenediammonium sulfate were used as "tailor-made" additives to direct the mirror-symmetry breaking in the attrition-enhanced deracemization (i.e. Viedma ripening) of conglomerate crystals of ethylenediammonium sulfate (EDS). Isothermal titration calorimetry (ITC) shows chiral recognition of (1R,2R)- and (1S,2S)-1,2-diphenylethylenediamine to EDS crystals where the enthalpy of adsorption of the (1R,2R)-isomer on l-EDS crystals is higher in comparison to that on d-EDS crystals. These results are consistent with a "rule of reversal" mechanism driving the chiral outcome of the Viedma ripening of EDS.

Original language	English
Pages (from-to)	12626-12629
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	85
DOIs	https://doi.org/10.1039/c6cc06534a
State	Published - 18 Oct 2016

All Science Journal Classification (ASJC) codes

Electronic, Optical and Magnetic Materials
General Chemistry
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Catalysis

Access to Document

https://doi.org/10.1039/c6cc06534a

Cite this

@article{3d1425ce6ecb44f8a8ca037d5dd4ac30,

title = "Directing the Viedma ripening of ethylenediammonium sulfate using {"}: Tailor-made {"} chiral additives",

abstract = "Both enantiomers of trans-cyclohexane-1,2-diammonium sulfate and trans-1,2-diphenylethylenediammonium sulfate were used as {"}tailor-made{"} additives to direct the mirror-symmetry breaking in the attrition-enhanced deracemization (i.e. Viedma ripening) of conglomerate crystals of ethylenediammonium sulfate (EDS). Isothermal titration calorimetry (ITC) shows chiral recognition of (1R,2R)- and (1S,2S)-1,2-diphenylethylenediamine to EDS crystals where the enthalpy of adsorption of the (1R,2R)-isomer on l-EDS crystals is higher in comparison to that on d-EDS crystals. These results are consistent with a {"}rule of reversal{"} mechanism driving the chiral outcome of the Viedma ripening of EDS.",

author = "Nguyen, {Thi Phuong Thao} and Cheung, {Pui Shan Monica} and Liora Werber and Jacinthe Gagnon and Reajean Sivakumar and Cameron Lennox and Aaron Sossin and Yitzhak Mastai and Cuccia, {Louis A.}",

note = "Publisher Copyright: {\textcopyright} 2016 Royal Society of Chemistry.",

year = "2016",

month = oct,

day = "18",

doi = "https://doi.org/10.1039/c6cc06534a",

language = "الإنجليزيّة",

volume = "52",

pages = "12626--12629",

number = "85",

}

TY - JOUR

T1 - Directing the Viedma ripening of ethylenediammonium sulfate using "

T2 - Tailor-made " chiral additives

AU - Nguyen, Thi Phuong Thao

AU - Cheung, Pui Shan Monica

AU - Werber, Liora

AU - Gagnon, Jacinthe

AU - Sivakumar, Reajean

AU - Lennox, Cameron

AU - Sossin, Aaron

AU - Mastai, Yitzhak

AU - Cuccia, Louis A.

PY - 2016/10/18

Y1 - 2016/10/18

N2 - Both enantiomers of trans-cyclohexane-1,2-diammonium sulfate and trans-1,2-diphenylethylenediammonium sulfate were used as "tailor-made" additives to direct the mirror-symmetry breaking in the attrition-enhanced deracemization (i.e. Viedma ripening) of conglomerate crystals of ethylenediammonium sulfate (EDS). Isothermal titration calorimetry (ITC) shows chiral recognition of (1R,2R)- and (1S,2S)-1,2-diphenylethylenediamine to EDS crystals where the enthalpy of adsorption of the (1R,2R)-isomer on l-EDS crystals is higher in comparison to that on d-EDS crystals. These results are consistent with a "rule of reversal" mechanism driving the chiral outcome of the Viedma ripening of EDS.

AB - Both enantiomers of trans-cyclohexane-1,2-diammonium sulfate and trans-1,2-diphenylethylenediammonium sulfate were used as "tailor-made" additives to direct the mirror-symmetry breaking in the attrition-enhanced deracemization (i.e. Viedma ripening) of conglomerate crystals of ethylenediammonium sulfate (EDS). Isothermal titration calorimetry (ITC) shows chiral recognition of (1R,2R)- and (1S,2S)-1,2-diphenylethylenediamine to EDS crystals where the enthalpy of adsorption of the (1R,2R)-isomer on l-EDS crystals is higher in comparison to that on d-EDS crystals. These results are consistent with a "rule of reversal" mechanism driving the chiral outcome of the Viedma ripening of EDS.

UR - http://www.scopus.com/inward/record.url?scp=84992220406&partnerID=8YFLogxK

U2 - https://doi.org/10.1039/c6cc06534a

DO - https://doi.org/10.1039/c6cc06534a

M3 - مقالة

C2 - 27722259

SN - 1359-7345

VL - 52

SP - 12626

EP - 12629

JO - Chemical Communications

JF - Chemical Communications

IS - 85

ER -

Directing the Viedma ripening of ethylenediammonium sulfate using ": Tailor-made " chiral additives

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this